


Adventures at Sandover

by supernaturallylost



Category: Supernatural
Genre: Affection, Aftercare, Alternate Universe - Office, Anal Sex, Begging, Biting, Blow Jobs, Bottom Dean, Butt Plugs, CEO Castiel, Castiel is a Little Shit, Cock Warming, Comeplay, Coming Untouched, Dirty Talk, Dom Castiel, Dom/sub, Elevator Sex, Enthusiastic Consent, Episode: s04e17 It's a Terrible Life, Eventual Smut, Exhibitionism, Fluff, Gentle Dom Castiel, Gentle Sex, Gentleness, Hair-pulling, Hand Jobs, Hurt/Comfort, Intimacy, Lipstick & Lip Gloss, M/M, Makeup, Master/Pet, Masturbation, Mutual Pining, Office Sex, Other Additional Tags to Be Added, Panty Kink, Partners to Lovers, Pining Dean, Porn with Feelings, Possessive Castiel, Possessive Sex, Praise Kink, Quiet Sex, Restraints, Rimming, Romantic Fluff, Rough Sex, Roughness, SO MUCH FLUFF, Safeword Use, Scratching, Semi-Public Sex, Sick Dean, Smut, Smut and Fluff, Some Plot, Spanking, Stress Relief, Sub Dean, Tie Kink, Top Castiel, Voyeurism, Worried Castiel, Wrists
Language: English
Status: In-Progress
Published: 2015-09-08
Updated: 2016-06-23
Packaged: 2018-04-19 17:01:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 13
Words: 33,833
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4754111
Author URL: https://archiveofourown.org/users/supernaturallylost/pseuds/supernaturallylost
Summary: <blockquote class="userstuff">
              <p>It starts with an interview with Mr. Adler, and it ends with Mr. Novak and the most awkward encounter of Dean's life. This is the story of a young Sandover employee, Dean Smith, and his seductive boss, Castiel Novak. Their relationship is certainly an adventure.</p>
            </blockquote>





	1. The Job Offer

**Author's Note:**

  * For [lyster99](https://archiveofourown.org/users/lyster99/gifts).



Dean Smith aligned his resume with his letters of recommendation inside of his manila folder. He tucked it securely into his briefcase, straightened his red tie around his neck, and nodded to his reflection in the mirror in the hallway of his apartment. A quick glance out of the window led him to pick up his rain jacket, throwing the black coat over his arm easily before opening the door and walking out.

On his way to the interview, Dean held his head high in the air except for the several moments he checked his watch to make sure he was still ahead of schedule. Quickly, but not necessarily with the droll urgency of those around him, Dean glided over the busy streets for another two blocks until he found the café. Standing at the podium beside the door was a hostess in a white blouse and a black pencil skirt.

“Hello, sir,” she smiled as he approached her with a smile. “How may I help you?”

“I’m a little early,” Dean grinned with an apologetic shrug, “for a meeting with Mr. Adler. Is it too soon for the reservation?”

“Not at all!” she nodded. “Mr. Adler actually arrived only a minute before you. Are you ready to be taken to his table?”

Dean laughed nervously, but gestured forward.

“Lead the way,” he asked politely.

With a short, appreciative nod, the woman walked ahead of Dean and led him inside just as the sky opened up to release a small drizzle of rain. When they arrived near the back of the well-lit café, Dean saw a balding, portly man in a neat suit complete with a purple and gray tie. He sat with his hand around the handle of a dainty teacup until he saw the pair walking toward him.

“Mr. Adler,” the hostess nodded, “your other party member has arrived.”

“Thank you, Lisa,” the man said with an easy, light-hearted voice. While the hostess left the two of them alone, he smiled, stood from his chair, and reached for Dean’s hand. “Pleasure meeting you, Mister Smith.”

“You as well, Mister Adler,” Dean grinned.

“Go ahead and have a seat here, and we’ll get started,” Mr. Adler waved to the chair opposite him. “I’ve read over your resume and contacted some of your previous employers, and I must say. I’m very impressed.”

“Well thank you very much,” Dean nodded. He set down his briefcase, unbuttoned the bottom button of his suit jacket, and sat down. “I’ve worked very hard to try to find an opportunity like this, so thank you for agreeing to meet with me.”

Mr. Adler half-smiled in response, clearly appreciative of Dean’s attitude. Indeed, as he sat and asked Dean about his strengths, weaknesses, goals, preferences, and skills, Mr. Adler only grew more and more comfortable with Mr. Smith’s relaxed tone and straightforward wording. By the time their interview neared its end, Mr. Adler was focusing more on the look of genuine kindness in Dean’s eyes than his story about his greatest accomplishment. Much to his surprise, he felt a little bit of affection forming already.

“It’s only a hobby, of course,” Dean concluded obliviously. He reached down and grabbed his coffee cup with a nod. “Still, it’s nice to have other things to do than data configuration or analysis.”

“I hear you,” Mr. Adler responded.

He raised his own tea cup in agreement. When they each finished their drinks, they sighed at the same time, earning a little chuckle from Mr. Adler.

“Well, Dean,” Mr. Adler grinned. “Can I call you Dean?”

“Yes, you may, sir,” Dean said happily.

“Well, Dean, I don’t see any reason why we wouldn’t want you working for us as soon as possible. You seem like a great addition to our team at Sandover, and I believe you’ll fit right in with the environment you’ll be working in.”

“I’d certainly look forward to finding out,” Dean laughed lightly.

“So, do you have any last questions for me?” Mr. Adler asked, watching Dean’s emerald eyes twinkle with pride.

“I do, actually,” Dean nodded. He’d learned very early on that the best thing to do during an interview was to ask questions. “Speaking of the environment I’ll be working in, the position listing was a little unclear about which department I’ll be working under. I’m wondering if it’s going to be an interdepartmental position or if I’ll be working mainly with one or the other.”

“Fair question,” Mr. Adler responded. “As of this moment, you’ll be working under my department of statistical analysis, though you may also report to Mr. Novak’s department when needed. This may change later on, should you decide to join us.”

“Perfect,” Dean nodded. “I’m very flexible, so working with multiple bosses is definitely alright with me. What kind of person is Mr. Novak, if I can ask? If I’m going to work with him as well, I’d like to have some idea of his personality beforehand.”

“Of course,” Mr. Adler nodded. “Mr. Novak is the son of the company CEO, so he practically manages the entire building. Even I, at times, report to him. Because of all of his business taking up so much of his time, he’s a little bit drier than I am. He appreciates when people speak plainly, and he doesn’t care for overcomplicating anything. He’s a magnificent worker, and he’s very charitable. Everyone in the offices admires him. I’m sure the two of you will get along just fine.”

“Sounds great,” Dean answered, throwing his hands in the air a little bit. He sighed. “Well, that answers all of my questions, I think.”

“Well, then, I’d like to officially offer you a position with our company,” Mr. Adler said. He watched Dean’s eyes sparkle and ignored the butterflies in his stomach. “What do you say, Dean? Would you like to work at Sandover?”

“I’d love to,” Dean beamed.

Slowly, Mr. Adler stood up and reached out a hand. Dean stood, shook it, and grinned widely.

“Glad to have you on board, Mr. Smith,” Mr. Adler said. “I look forward to giving you the tour of the building tomorrow morning at eight.”

“Sounds perfect!” Dean answered.

 

At six in the morning, Dean Smith woke up, showered, and packed his salad and papers inside of his briefcase. He’d practiced shaking hands with the coat rack five times, winked at his own reflection twice, and drank one bottle of cleansing kiwi water before he finally made it out of the door in his favorite blue suit and red tie.

His apartment was perfectly located in relation to the big, glass offices of Sandover. On days with good weather, including this particular morning, he could walk there in ten minutes without even breaking a sweat. So, briefcase in hand, he took the walk to his new work. Though he still did not walk quite so hurriedly as those around him, he did move faster than normal to get rid of some of his nerves. By the time he reached the clerk’s desk inside the building, he was practically anxiety free.

“Good morning, sir,” the receptionist smiled politely. “What can I do for you this morning?”

“Could you please tell Mr. Adler that Dean Smith is here?” Dean asked.

“One moment,” she responded.

While she got a hold of his boss, Dean looked around the lobby. People were just filing into work in their suits or their yellow tech support polos. Dean was gazing at one particularly calm looking man in a blue tie and a trench coat when the receptionist informed him that Mr. Adler would be down presently.

“Thank you,” Dean smiled, looking back in time to see the man enter an elevator on his own.

Just as the doors to the elevator closed, the man looked up. His dark hair shifted from his face and Dean could tell, even from that distance, that he was looking directly at him. The gaze made something in Dean feel eager, though he didn’t understand quite what. Before he could give it much thought, Mr. Adler interrupted his thoughts with another handshake.

“Good morning, Dean,” he grinned. “Good to see you! Let’s get started on our tour!”

While they waited for an elevator, Dean glanced at the one the stranger had gone through. Beside was a sign marking it as a private elevator.

“That,” Mr. Adler said when he noticed Dean looking, “is the private Novak elevator. The CEO and his family are allowed to use it, as well as the occasional business partner or associate upon request. I’ve taken that elevator once, when I was initially hired by Mr. Novak senior.”

“Is it any different than these?” Dean asked genuinely.

“Hardly,” Mr. Adler shrugged. “There’s a handle on the ceiling and a slightly padded floor. It seems a little over cautious to me.”

Just then, the public elevator dinged and the both of them entered.

“So, while you’re here, there are three major floors you’ll want to know about. The others I’ll leave you to take a peek at on a break if you’re curious, but they’re only human resource offices and other essential data supply offices. You’ll be more interested in floors four, seven, and eight. Floor four is the call center where you’ll find the largest break room, though there is one on every floor. Most people use the breakroom on floor four because of the space and because it’s home to our Information Technology Department. Calls from inside the company, and from our sister offices in other cities, that require technical assistance are sent to the call center, and our professionals try to help as much as possible.”

“That’s not a job I’d like to do,” Dean laughed. “It takes a lot of specific training to be able to work with computers the way IT can.”

“True,” Mr. Adler nodded. “Floor seven will be your floor. The departments of analysis are split between seven and eight. I mostly keep to floor seven and Mr. Novak junior mostly stays on floor eight, though there are, of course, exceptions. You’ll mainly be staying on floor seven, unless Mr. Novak needs your assistance at point.”

“Understood,” Dean said.

“Excellent! I suppose we’ll take a quick walk around each of the three floors I mentioned and then I’ll go introduce you to Mr. Novak.”

 

The break room was surrounded by glass windows, but blinds could be pulled down to give it more privacy. Sometimes, Dean was told, there are impromptu private meetings in the breakroom when the other conference areas are full, so it’s not unusual for the blinds to be closed and the door to be locked. If that’s the case, the break room on floor two would be an adequate space to use.

On the seventh floor, Dean was introduced to several workmates whose names became a blur soon after. He also saw the copy room, which was small, crowded, and smelled of ink. The glass windows that were supposed to make it feel open were taken over by stacks of spare paper and notices that had misspellings or other errors.

Finally, Dean felt nervous tingles in his toes and fingers as Mr. Adler pressed the button for the eighth floor. The much anticipated meeting with Mr. Novak approached along with gentle, soothing elevator music.

“You’ll be pleased to see that there is a small lounge on this floor,” Mr. Adler grinned as the door opened. “Oftentimes, when employees need to work overtime for some reason, they prefer to sit on the sofas here rather than at their desks. You’re welcome to use the lounge freely after hours, but we do ask that during hours, only clients and business partners here to see Mr. Novak use the area.”

“Certainly,” Dean nodded.

The elevator doors opened to a brown reception room that was very modern and up-to-date. Dean noted that most business partners would only ever see this floor, so naturally it should look the best of them all. To his right, he saw the lounge, already with two people sitting with tablets out on their laps.

“You might also simply be more comfortable in your office,” Mr. Adler smiled, catching Dean’s eye. “The corner offices are all slightly more comfortable than the rest, though slightly smaller.”

“It did look welcoming,” Dean agreed. “I’d expected it to be more open, but it’s right at the end of the hall.”

“Yes, but if you leave your door open during the day, people will drop by to visit and communicate just as much as if you were in the center of the hallway. If you’d prefer to switch, we can see about the change. I’m not saying it’s possible, but we could certainly find out.”

“No,” Dean waved his hands. “The corner office suits me, I think. I just wasn’t expecting so much privacy.”

Mr. Adler nodded as they walked down the hallway toward a wall of windows. There, Dean looked down at the view of the city. He could almost see his apartment building from where he stood.

“It’s beautiful here,” Dean noted.

“Yes, it is,” Mr. Adler agreed. After a small moment of silence to let Dean enjoy the view, he cleared his throat. “To our right here is the main conference room. There is a monthly meeting for the department leads, and a weekly meeting for individual departments. You will attend the weekly meetings with both myself and Mr. Novak so that we can regroup and make sure we’re all working like a well-oiled machine.”

“Sounds reasonable,” Dean approved.

He eyed the conference room with a raised eyebrow. The room was enclosed with glass, and there were currently people inside looking at graphs and charts of recent profits.

“And to the left,” Mr. Adler continued, “is Mr. Novak’s office. If he calls you up, it’s a straight walk from the elevator all the way to the end.”

Dean looked at another glass enclosed room, though this one was made private with proper navy blue curtains.

“The drapes aren’t always closed,” Mr. Adler explained. “Only when Mr. Novak is expecting a meeting will he close the curtains for more privacy. Otherwise, he likes to keep them open so his office feels approachable to everyone.”

“You did say people admired him,” Dean nodded. “That must be part of the reason.”

Mr. Adler nodded, stepped forward, and knocked on Mr. Novak’s door.

“Come on in, Mr. Adler,” a raspy voice answered.

Mr. Adler opened the door, held it for Dean, and then closed it behind them. The room was large, filled with an impressive desk, a wall of bookshelves, and a small sitting area with a wood coffee table. From across the room, Mr. Novak stood, buttoned his suit jacket, and stepped around his desk.

“Mister Smith, this is Mister Novak.”

Dean tried not to react, though he recognized that gaze from earlier. Again, something stirred in his gut. He covered the strange reaction with his usual charm, and he easily held eye contact with those icy blue eyes. When Mr. Novak stepped forward, his dark hair out of his face and his stubble casting just the perfect shadow on his face, Dean stepped forward to meet him, reaching his hand out a little too eagerly.

“Mister Smith,” Mr. Novak nodded. He caught Dean’s hand easily, and Dean noticed how soft the man’s skin was. Dean almost didn’t want to let go. “I’ve heard good things about you.”

“I hope I can live up to them, Mister Novak,” Dean answered, stuck a little bit in the secret smirk starting to form on the man’s mouth. Meanwhile, he felt a brush of Mister Novak’s fingers against the back of his hand just before he released his hold. Hesitantly, but with his usual easygoing tone, Dean added, “I’ve been told that I’ll be working with you on occasion in addition to reporting to Mr. Adler.”

“That’s our intention at the moment,” Mr. Novak nodded, keeping his eyes evenly on Dean. “We may have to adapt as needed, with you either seeing Mr. Adler or myself more often.”

For some unknown reason, Dean felt the tops of his ears go warm.

“Well, Mr. Novak,” Mr. Adler interrupted obliviously, “we should let Mister Smith get perfectly situated in his office now, don’t you think?”

“Certainly,” Mr. Novak answered, his eyes even still on Dean. He smiled softly, secretively. “I hope you enjoy your day today, Mister Smith, and I look forward to seeing you again soon.”

It took Dean a second to realize that Mr. Adler was gesturing for him to leave the office. When he did realize, he awkwardly coughed and scratched the back of his neck before giving a one handed wave to Mr. Novak and leaving the room. He thought he heard a soft, breathy laugh behind him.

“So, what did you think of Mr. Novak?” Mr. Adler asked as they walked toward the elevator.

“He’s fascinating,” Dean answered. He looked back down the hall toward Mr. Novak’s office as the elevator doors closed. “I look forward to working for him.”


	2. Settling In

**Summary for the Chapter:**

> Mr. Smith is called up to Mr. Novak's office near the end of the day for a very important meeting.

**Notes for the Chapter:**

> From now on, the kinks/styles will be listed specifically at the beginning of the chapters so you know what to expect. In this chapter, for example, there's a blowjob, rimming (coming from that alone), begging, and a bit of a praise kink. Fairly mild, overall.

By the end of the day, Dean was already content sitting at his desk in the corner office and learning the company’s computer system. Five o’clock drew ever nearer, but before it came, Dean heard his phone ring.

“This is Dean Smith,” he answered.

“Hello, Mister Smith,” came a low voice. Mr. Novak had a smile in his voice, despite the urgent tone. “I need to see you in my office immediately.”

“Yes, sir,” Dean responded, dropping the receiver and straightening his red tie.

He stood, took a deep breath, momentarily wondered if he’d done something wrong, and then noticed the goose bumps on his neck and arms. Mentally reassuring himself, he made his way to the elevator to press the button for one floor higher. The walk to Mr. Novak’s office seemed longer than it had earlier, and this time there was something about the curtains being closed that made Dean shiver.

Gently, Dean knocked on the door. When he heard Mr. Novak’s voice, he entered the room.

“Um, Mr. Novak, sir, you wanted to see me?” Dean managed to say.

Sitting with his legs crossed in the leather armchair of his sitting area was Mr. Novak. He let a magazine fall from his hands and land on the coffee table before standing and walking over. He passed Dean and went to the door, slowly closing it behind him.

“Ah, yes, Mr. Smith,” he smiled. He turned back to meet Dean’s nervous eyes. “Or Dean?  May I call you Dean?”

“Of course, Mr. Novak,” Dean answered. He cleared his throat and added a hesitant, “sir.”

Mr. Novak’s eyes smiled, but his lips gave nothing away.

“How has your first day been, Dean? Anything I need to be made cognizant of?” Mr. Novak stood with his hands clasped calmly in front of him.

“No, sir,” Dean answered with a lick of his lips. “Everyone has made me feel like a very welcome part of the team.”

Mr. Novak nodded and walked around Dean, who remained frozen in place.

“And all your needs have been met?” Mr. Novak asked quietly.

Dean felt the hairs on the back of his neck raise while Mr. Novak walked casually behind him. Dean stared forward without knowing what to say.

“Your office is satisfactory?” Mr. Novak clarified.

“Oh yes, sir,” Dean sighed with relief. He cleared his throat again and licked his lips. “Very satisfactory.”

“There is nothing else you might require?” Mr. Novak asked, stepping closer from behind. Dean felt goose bumps rise all along his neck and arms. Gently, Mr. Novak leaned over Dean’s shoulder and breathed into his ear. “Perhaps something with a more personal touch?”

“Oh,” Dean gasped quietly. He cleared his throat once more. This was his chance, he knew. “I think I might need something like that, now that you mention it.”

“Tell me, Dean,” Mr. Novak whispered, his hands suddenly sliding gingerly over Dean’s wrists and his breathy laugh tickling Dean’s neck. Dean had the suspicion that Mr. Novak was laughing at his accelerated pulse. “What do you need, Dean?”

Dean faced forward and swallowed hard. All of the sudden, Mr. Novak’s lips were on his neck, lightly placing kisses against his pulse point there. Dean leaned his shoulder back to make his neck more accessible. He closed his eyes.

“I need you, sir,” Dean answered breathily. “I need you to touch me.”

Mr. Novak’s hands snaked around Dean’s chest and brushed over his nipples on their way to his tie.

“Oh,” Dean gasped again.

“Quietly, Dean,” Mr. Novak warned. “We must stay quiet for these last few minutes of the work day.”

Dean bit his lips while Mr. Novak pressed against him from behind. Even through his pants, Mr. Novak’s erection was pushing against Dean. Dean shivered. While kissing his neck calmly, Mr. Novak gently unknotted Dean’s tie, pulled it free, and tossed it onto the coffee table. Dean let go of a shaky breath he didn’t realize he’d been holding.

“Do you like the environment here, Dean?” Mr. Novak asked with a smile. He began slowly unbuttoning Dean’s shirt from behind, gently grinding his hips into Dean. Dean could do nothing but remain still.

“God yes,” Dean whispered. When Mr. Novak’s hands stopped, Dean quickly added, “sir.”

Another soft, knowing laugh left Mr. Novak’s lips. Dean’s shirt was still tucked into his pants, a problem Mr. Novak seemed excited to solve. He began undoing Dean’s belt.

“Please,” Dean whispered suddenly.

“Yes, Dean?” prompted Mr. Novak. “What is it?”

“Let me help,” he answered.

Mr. Novak hummed approvingly against Dean’s neck. Then he let go of him and stepped back.

“Clothes off, Mr. Smith,” he ordered, “including your socks, please.”

Dean hurried to comply and turned to look at Mr. Novak, who was watching with lustful eyes. Dean shivered and took off his pants, socks, jacket, and shirt. He was standing in only his underwear when he hesitated. The tops of his ears were red with embarrassment. He felt foolish, standing there mostly naked waiting for reassurance.

“That’s alright,” Mr. Novak whispered gently. He stepped forward again, lifting Dean’s chin so they met eyes. “It’s okay that you hesitate to obey me now. You’ll learn, won’t you?”

“Yes, sir,” Dean answered, his dick bulging conspicuously between them.

“You’ll try your very hardest to do what I ask of you, won’t you?” Mr. Novak said, his eyes boring into Dean’s. In his eyes was the very clear choice. Dean could say yes, or he could say no and never be bothered again. “Won’t you, Dean?”

“Yes, Mister Novak, sir,” Dean answered enthusiastically. “I’ll learn to obey.”

Mr. Novak smiled softly and hummed with approval. Then he took a deep breath.

“Do you want to show me how quickly you can learn?” Mr. Novak asked easily, letting go of Dean’s face.

“Please, sir,” Dean nodded. “Yes, sir.”

“Then clothes off, Mister Smith.”

Dean reached down and removed his underwear, revealing a hard, already leaking cock. Dean almost shook when he saw Mr. Novak’s reaction. His jaw tensed and his eyes scanned Dean’s body greedily.

“I want you to take off my pants now, Dean,” Mr. Novak instructed, his voice even. “Can you do that?”

Dean nodded eagerly and articulated a slightly loud, “Yes please, sir.”

“Ah, be quiet now,” Mr. Novak said, pressing a finger to his lips. “Kneel down, take off my pants, and stay silent.”

Dean immediately fell to his knees in front of Mr. Novak, and his fingers fumbled over the belt and the zipper of Mr. Novak’s pants. Soon enough, the pants were dropped to the floor in a heap and Dean was staring at a pair of satin boxer shorts with a very large bulge in the middle.

“Use your mouth,” Mr. Novak whispered.

Dean hastily leaned forward, pressing his mouth to the band of Mr. Novak’s underwear. Gently, he let his cheek brush against Mr. Novak’s cock before shivering and biting on the fabric near his hip. It took a few moments of shimmying the band down, but eventually, Dean was rewarded with the sight of a shiny, red, leaking cock sticking forward toward his watering mouth.

“You’re doing well, Mister Smith, so I’ll give you a choice,” Mr. Novak praised quietly. “Do you want to suck me off, or do you want me to bend you over my desk?”

Dean let out an involuntary whine from the back of his throat. Through his eyelashes, he looked up at Mister Novak’s half-smile. Still in his suit jacket, shirt, and tie, Mr. Novak looked like every dream Dean never dared to have.

“Please, sir,” Dean groaned. “I want both.”

Mr. Novak shook his head and said simply, “Feeling greedy, aren’t you, Dean?”

Dean nodded and moved forward a little bit.

“You can’t have both,” Mr. Novak said. “At least, not right now. I want you to taste me. You need to know how I taste before you decide if you want to continue this little relationship of ours. We’ll have plenty more chances to have you bent over my desk trying not to scream. Is that okay with you, Dean?”

Dean nodded, managed a weak, “Yes sir,” and let Mr. Novak’s hands wrap in his hair.

“Good boy,” Mr. Novak whispered. Dean tried to stifle his whine, but it rose to his lips anyway. “So good, Dean.”

Dean stared at the thick, dripping cock in front of his eyes. His mouth watered and he had to bite his tongue.

“Go ahead, Mister Smith. Suck.”

Without a second’s hesitation, Dean rushed forward with his mouth wide. He felt Mr. Novak’s hands tighten in his hair, but he didn’t push his head at all. He left the work to Dean. Happily, Dean kissed the head of Mr. Novak’s cock before hollowing out his cheeks and sucking him down, little by little. When Dean moaned involuntarily, Mr. Novak tugged his hair.

“Quietly, Mister Smith,” Mr. Novak ordered. He added darkly, “I won’t remind you again.”

Dean breathed hard before letting his tongue twist under and around Mr. Novak’s cock. He bobbed his head forward and back, sucking as much of the cock as he could. Though he couldn’t fit the whole length in his mouth, he enjoyed playing with what he could.

Tentatively, Dean let his hands slide up Mr. Novak’s thighs. While he tongued the slit of Mr. Novak’s cock, he silently asked permission to touch his body.

“Yes,” Mr. Novak groaned hoarsely. “Yes, you may, Mister Smith.”

Dean immediately trailed his hands around the base of Mr. Novak’s cock before landing on his balls. He turned his head to get a better angle, swiped his tongue down and up the underneath of his cock, and ran his fingers easily over Mr. Novak’s balls and perineum.

“Good boy,” Mr. Novak praised. His head was thrown back and his hands were smoothing appreciatively down Dean’s neck. “You’re so perfect, Dean.”

Dean’s cheeks hollowed out again and he pulled a long sigh from Mr. Novak.

“Yes,” he whispered. “Yes.”

Dean continued playing with Mr. Novak’s body, sucking him down as much as he could, and breathing through his nose. Eventually, Mr. Novak’s body tensed and his finger clenched around Dean’s hair. He didn’t move, but Dean could practically feel him wanting to pound into Dean’s mouth. Now Dean bobbed his head faster, eagerly trying to fit as much of his boss into his mouth as possible.

“Ah,” Mr. Novak said involuntarily. He bit his lip, squeezed his eyes closed, and breathed quickly through his mouth. “Oh!”

All of the sudden, he felt himself coming, hard and hot, into Dean’s mouth.

Dean breathed unevenly through his nose as he eagerly swallowed the salty, tangy taste of Mr. Novak. He let his hand move along the center of Mr. Novak’s cock while he moved to wrap his tongue around the head. He sucked down everything Mr. Novak gave him, pumping him in his fist until he heard a soft sigh above him.

“Oh, Dean,” Mr. Novak sighed, reaching to pull Dean away. “Oh, so perfect, Mister Smith.”

Dean beamed up at him proudly, watching those wide, alert eyes that smiled down at him.

“Please, sir,” Dean whispered. He looked down at his aching cock. It was dripping all over Mr. Novak’s carpet.

“Okay, Mister Smith,” Mr. Novak whispered. “You’ve been so good for me. Go lay down on the coffee table.”

Dean stood from his red, sore knees and rushed over to the large, wooden table. He knocked the magazines from it and lay down on his back. In front of him, he saw Mr. Novak chuckle.

“We’ll have to work on not making a mess, won’t we, Mister Smith?” Mr. Novak smiled.

Dean nodded quickly, spread his legs, and waited for whatever Mr. Novak would give to him.

“Eager?” Mr. Novak asked amusedly. When Dean nodded again, Mr. Novak walked forward, knelt beside the table, and ran his hands over Dean’s thighs. “I’m not going to suck you, Mister Smith. I’m going to get acquainted with that beautiful ass of yours. You’re going to be quiet, Mister Smith, and you’re going to come when I tell you to.”

Dean shivered, nodded, closed his eyes, and bit his tongue.

“I need you to lay on your stomach now, Mister Smith,” Mr. Novak said simply.

Dean flipped over without any effort.

Immediately, hands were kneading the softest parts of Dean’s flesh. Dean felt himself being massaged gently, hands wandering almost scientifically over his middle. Next, he felt the sensation of something wet along the very bottom of his left cheek. Soon after, teeth grazed over the skin there.

“Oh!” Dean said loudly. He froze when he realized his transgression.

“We’ll let that one slide,” Mr. Novak whispered. “I’ve sent my secretary out early this evening, so there’s not harm right now. You’ll need to learn to control yourself, Mister Smith.”

“Yes, sir,” Dean answered. “I will, sir.”

“For now,” Mr. Novak answered, his hands sliding over Dean’s ass, “bite into your arm if you want to make noise. Do you understand?”

“Yes, sir,” Dean whispered. He moved an arm under his mouth and closed his eyes.

Again, Mr. Novak’s mouth pressed over his skin, raising goose bumps of excitement. Mr. Novak took his time dragging his tongue down and around Dean’s crack. Dean was already biting hard into his forearm when he finally felt Mr. Novak’s tongue against his hole.

“Are you clean, Dean?” Mr. Novak asked gently.

Dean blushed and answered, “Yes, sir. Since my lunch break, sir.”

Mr. Novak raised an eyebrow and waited.

“I, um,” Dean hesitated. “I fingered myself, sir. I went home for lunch and took a short shower.”

Dean’s face was burning when he heard the soft laugh from behind him.

“You live close by?” Mr. Novak asked, grinning.

“Yes, sir,” Dean answered.

Mr. Novak hummed a moment before resuming his exploration. He pressed against Dean with his tongue, getting a feel for the puckered skin there before entering into Dean’s warm, tight hole.

“Ah,” Dean whimpered against his arm. “Oh.”

Mr. Novak’s hands pushed from the bottom of Dean’s cheeks to the top, spreading him out while he dived deeper inside with his tongue. Experimentally, he let his teeth press against Dean, who almost came at the sensation.

“Please, sir,” Dean whined quietly. “I’m so close.”

As if he’d heard nothing, Mr. Novak pressed into Dean again and again with his tongue, feeling around.

“Please!” Dean begged, he back arching slightly, pushing Mr. Novak closer and deeper.

Mr. Novak laughed breathily, leaned back, and wetted his finger quickly in his mouth.

“You’re so good, Mister Smith,” Mr. Novak smiled. “You’re going to come from my finger, aren’t you?”

“Yes,” Dean begged. “Yes, sir. Please, sir!”

“Just a little more, Dean,” Mr.Novak grinned. He pressed his wet finger into Dean slowly, moving it in and out slowly before moving faster and faster. He felt around Dean’s hole, inside and out, and tried to memorize which spots were the most sensitive. “You’re so perfect, Dean. I might let you come soon.”

“Oh!” Dean groaned against his arm.

He was biting into his skin hard enough to taste blood, but he didn’t even notice. All he knew was that the pleasure was building and building to the point that he thought he would pass out from the bliss of it. Finally, he heard the command whispered softly, easily, and hoarsely.

“Come.”

Dean obeyed, clenching his fists and tightly shutting his eyes. He shouted around his arm, making muffled noises of pleasure as bursts of hot, wet release fell onto the carpet.

“Good boy,” Mr. Novak was saying over and over. “So good, Dean.”

Dean whimpered while he came. When he opened his eyes, he was breathing shallowly, seeing black spots in his vision, and lying there totally incapacitated.

Mr. Novak stood up, cleared his throat, and walked over to the chair in front of Dean’s face. Dean looked up at him through a cloud of bliss, gazed up and down his relaxed, half-naked body, and smiled.

“So, Mister Smith,” Mr. Novak smiled wickedly. “Shall we discuss your work ethic?”


	3. Work Ethic

**Summary for the Chapter:**

> It starts with a conversation and ends with three days of agony.

**Notes for the Chapter:**

> Kinks: (graphic) fantasies, minimal restraint using a tie, thoughts of/resistance to masturbation, blow job

Mr. Novak leaned forward. His eyes scanned over the naked body in front of him. Dean, meanwhile, breathed deeply until he felt able to move. Eventually, he managed to prop himself up on his elbows and look at the damage he’d done to his arm and the carpet.

“I’m so sorry, sir,” Dean spoke quietly. He stared at the mess of come interrupting the blue, green, and red pattern of the Persian rug. “I think I’ve ruined your carpet.”

Mr. Novak only smiled, shrugged, and said, “I will have the cleaning staff take care of it in a few moments.”

Dean flushed a bit, painfully aware of the sweat layering his skin, the bleeding scratch on his forearm from his teeth, and the pleasurable throbbing of his ass.

“Dean,” Mr. Novak laughed softly. “Do you want to get dressed?”

Dean nodded slowly, unsure if he would be allowed to put his clothes back on. Luckily, he saw Mr. Novak grin, stand, and wave his hand in the direction of their clothes.

“Bring me mine as well, please,” he asked softly.

Glancing up through his eyelashes, Dean handed Mr. Novak his pants, boxer shorts, and belt. In a slightly awkward silence, the two of them dressed. Finally, when they were both looking almost the same as when Dean had first entered the room, Mr. Novak stepped forward. He put his hands along Dean’s elbows and guided him a little closer.

Mr. Novak had just opened his mouth to speak when the phone on his desk rang. Dean saw the unexpectedness of the interruption clearly in his eyes, but Mr. Novak composed himself quickly and walked over to pick up the black receiver.

“Hello, this is Castiel Novak,” he answered in his usual calm, low voice. Dean’s neck prickled with intrigue at the sound. “Yes, of course. Right away.”

Mr. Novak dropped the receiver slowly, turned to smile at Dean, and shook his head.

“This is going to be an important meeting that I can’t avoid,” he explained. “Can we discuss this later?”

Dean’s eyes wandered from the slightly out of place hairs sticking up from the top of Mr. Novak’s head to his perpetually amused eyes and his smirking lips.

“Yes, sir,” Dean answered distractedly.

“Dean,” Mr. Novak smiled, “you only have to call me sir when you’re on the clock. The work day is over now. You can call me by my name, if you’d like.”

“Yes, Mr. Novak,” Dean responded hesitantly. Mr. Novak raised his eyebrows and waited. “Um, Castiel.”

Castiel nodded appreciatively before gesturing to the door.

“You’re free to go now, Dean,” he said. “I’ll schedule another meeting with you tomorrow so we can discuss this.”

Dean’s thighs tensed momentarily before he nodded.

“That sounds perfect, sir,” he said. “I mean, uh, Cas.”

Cas chuckled softly and turned his back. While he walked to his desk and picked up the telephone, Dean bit his lip to keep from grinning like an idiot. He caught Cas’s eye one last time, waved just as awkwardly as before despite being deliberate this time, and made his way to the door. The entire walk to the elevator served to remind him of just how sore his knees were, and just how much sorer he wanted them to be.

 

As usual, Dean’s alarm went off at six in the morning. He followed his routine with a bit more zeal than usual, scrubbing extra hard with the soap in the shower, rinsing extra long with his mouthwash over the sink, and drinking an extra glass of his cleansing kiwi water before packing a salad for his lunch along with the files he needed for his second day of work. He even whistled when he left the apartment, excited to start his Friday morning.

His walk to work on this particular morning was fast-paced, prepared, completely confident, and, for the first time in his life, just as urgent as those walking around him, though likely for a different reason.

When he arrived at his office building, he walked directly to the public elevator, slid inside, and waited to reach the seventh floor. He grinned at his colleagues, waved to a few of them, and kept going until he reached his corner office. On his desk was a manila file with a blue sticky note on top.

“Confidential Material for Dean Smith,” he read on the note. “Please find inside the essential paperwork for your meeting with Mr. Novak this afternoon at 4:45pm.”

Dean raised an eyebrow, went back to close his office door, and sat down at his desk. His fingers moved too quickly for his mind to be aware of, and before he knew, the file was open. Dean stared at an index page indicating a section for safety and care, mutual respect and understanding, and the list of everything Dean might ever need from Mr. Novak. When he flipped the index page over, he smiled at the green sticky note that had Cas’s handwriting on it.

“Should you decide to agree to this, I require that you not only read what I have provided, but also your own additional research to be completed over the weekend.”

Below that sticky note was another.

“You will need to learn all of this by heart, and you will need to create a safeword. Please read about safewords in the following pages.”

Dean flipped through a few pages and found more sticky notes explaining what the information talked about. He then eagerly looked over the list. Spanking, possessiveness, plugs, gags… anything and everything Dean could ever want, as well as some things he never wanted, was on that list. Of course, on top of it all was a bright green sticky note.

“Mark these with green or yellow. Get rid of those you are uncomfortable with by striking through them.”

Dean pulled out a sharpie and some highlighters, turned back to the beginning, and impatiently began reading. With Mr. Novak’s notes to guide him, Dean settled in for a long morning of hard work.

Dean had only put in four hours of work before he heard a knock on his door.

“Come in,” he answered, stuffing all of his papers back into the file. When he looked up, a smiling balding man stood before him. “Mr. Adler! What can I do for you?”

“I was going to go down to the coffee shop in the lobby for lunch,” Mr. Adler smiled, oblivious to the blush along Dean’s neck. “I wondered if you’d like to join me.”

“Oh,” Dean said. He recovered his charm easily, however, and added, “I’d love to, sir. I could certainly use a break.”

“That’s what I thought,” Mr. Adler laughed. “You’ve been shut in your office all morning.”

Together, the two of them took the stairs down to the lobby, discussing the plan for this week’s budget reconfiguration.

“Mr. Novak seemed quite excited to have you working with us,” Mr. Adler said casually. “I have to say, he does seem impressed with you.”

Dean tried to shrug, but his shoulders were too tense. Instead, he only answered, “Mr. Novak was very supportive on my first day, so I’m just hoping that I can live up to his expectations.”

“Don’t worry,” Mr. Adler laughed, patting Dean on the back. “I’m sure you’ll be just perfect in every position he puts you in.”

When they reached the coffee shop, a man in a green hat took their orders.

“Thank you, Gabriel,” Mr. Adler smiled. “How’s the family?”

Mr. Adler continued with the small talk, though he caught sight of something from the corner of his eye. Just as Dean reached over to add nutmeg and cream to his coffee, his sleeve pulled away from his wrist, revealing a large bluish bruise on his forearm. Remaining calm through his growing concern, Mr. Adler looked from the marks on Dean’s arms to the smile on his lips.

“Here you are, sir,” Gabriel interrupted. “Anything else I can get for you?”

Mr. Adler shook his head, stunned into silence for a moment. He raised an eyebrow and watched Dean adjust his shirt to cover his wrist properly, look up grinning, and talk about his ideas for the budget rearrangement. Mr. Adler forced himself to act normal through lunch and the elevator ride back to work. Then, he said goodbye to Dean and continued to the eighth floor.

The next couple hours moved too slowly for Dean’s liking. By four o’clock, he was jittery, alternating between pacing and twiddling a pen between his fingers. Half an hour passed, each second moving a little faster than the last.

Unable to wait any longer, Dean collected his folder, straightened his red tie, and cleared his throat.

“Off to a meeting?” Mr. Adler asked while they walked by each other in the hallway.

“Mr. Novak asked me upstairs for a moment,” Dean responded happily, the tops of his ears warm with blush. “He gave me a classified project for today, so I suspect he’ll want to discuss the results.”

“Good luck,” Mr. Adler grinned. He glanced down at Dean’s covered forearm discreetly.

The instrumental music in the elevator included violins and trumpets. Dean felt comfortably nervous while tapping his heel to the ground and adjusting his shirt cuffs. He’d left the suit jacket at his desk this time to save some trouble.

After he nodded to Mr. Novak’s secretary, he thought about Mr. Novak’s wrists. They were smooth, strong, and dexterous. He closed his eyes and swallowed hard when he imagined those wrists bending while Mr. Novak’s palm lands forcefully on his hip. He imagined those wrists calmly, inflexibly supporting the weight of Dean’s thighs while he pounds into Dean over and over against the wall. Mr. Novak’s sleeves would be rolled up, his shirt unbuttoned and his blue tie lying flat against his chest. Dean imagined the sight, readjusted his belt, and knocked on the closed door of Mr. Novak’s office.

“Come in, please,” came Mr. Novak’s husky voice. Dean obeyed easily, closing the door quickly behind him. He tripped a little bit in the process, but managed to recover quickly. By the time he turned around, Mr. Novak was standing behind his desk and buttoning his suit jacket closed. “Good afternoon, Mister Smith.”

Dean licked his lips.

“I see you received your assignment for the day.” Mr. Novak gestured to the file in Dean’s hand. “May I?”

Nodding, Dean walked the file over and set it in Mr. Novak’s outstretched hand. He let his fingers just barely brush over Mr. Novak’s, testing.

“You may sit down, Mister Smith,” Mr. Novak spoke indifferently.

Dean looked around the room to see which chair was closest to him. Across from Mr. Novak’s desk was a short, navy blue chair with a small backrest and no arms. Dean took the seat and crossed his legs.

“Uncross the legs, please, Mister Smith,” Mr. Novak nodded. “I’d like you to spread your legs wide for me. I’d hate for you to hide such a delicious feature. I want to see you while we discuss this.”

Dean bit his tongue and put a leg on either side of the chair. Sitting like that stretched his pants over a very conspicuous bulge. Dean blushed a little bit, but it faded quickly when he saw Mr. Novak’s wrists bend while he opened the folder.

“Impala?” Mr. Novak asked. “Your safeword is going to be impala?”

“Yes, sir,” Dean nodded. “Is that alright, sir?”

Mr. Novak smiled, but didn’t answer. For the next five minutes, Dean sat with his legs stretched wide while Mr. Novak leaned against his desk reading. Occasionally, Mr. Novak would look up and make sure Dean was being both quiet and obedient. Finally, when Dean started to feel too neglected, Mr. Novak set down the folder.

“Mr. Adler,” Mr. Novak began with a sigh, “commented on something very interesting to me this afternoon, Dean.  Can you imagine what that might have been?”

“No, sir,” Dean answered. He raised an eyebrow and looked up at Mr. Novak’s dark smile.

“He told me that he’d observed some bruising along your forearm,” Mr. Novak spoke lowly. He leaned forward, peered at Dean’s right arm, and waited for Dean to roll up his sleeve. When Dean complied, Mr. Novak shook his head. “Mr. Adler was quite concerned about your private life, Mister Smith. Should he be concerned for you?”

Dean shook his head quickly. “No, sir, not at all.”

“It was very bad to worry him so unnecessarily, then, wasn’t it, Mister Smith?”

Mr. Novak smiled, but his eyes were dark, his pupils dilated. Dean immediately swallowed and licked his lips. Mr. Novak took a deep breath, stood straight, and slowly took off his tie.

“Stand up, Mister Smith, and put your hands behind your back.”

Dean stood up too quickly, knocked over his chair, and blushed down at it. Slowly, he bent over to set the chair upright before putting his hands behind his back.

“I’m going to tie your hands out of the way, Mister Smith,” Mr. Novak whispered. He leaned against Dean’s neck and pressed a kiss to the nape. “You’re going to be very quiet now, aren’t you, Mister Smith?”

“Yes, sir,” Dean answered quietly. He felt Mr. Novak’s tie wrap around his wrists and knot twice.

“You’re not going to worry anyone else here, are you, Mister Smith?” Mr. Novak asked against Dean’s ear. His teeth grazed over the earlobe.

“No, sir,” Dean responded immediately. “I’m not going to worry anyone.”

“Are you going to keep your private life private?” Mr. Novak prompted. He pressed another kiss to the back of Dean’s neck.

“Yes, sir,” Dean answered. “Of course, sir. I’m sorry, sir.”

“Kneel down, Mister Smith,” Mr. Novak demanded. “Open your mouth and be silent.”

While Dean dropped to his knees and stared, Mr. Novak walked in front of him, unfastened his pants, and let his cock out from his trousers. Mr. Novak was leaking, dripping readily, his cock hard and almost desperate. Mr. Novak himself, however, was completely in control of himself when he commanded Dean to suck.

“You’re going to earn my forgiveness for this transgression,” Mr. Novak explained. “You will take me as deeply as you can to show how sorry you are for letting Mr. Adler see your bruises. Do you understand?”

Dean nodded eagerly, shifted forward on his knees, and forgot for a moment that his hands were tied behind his back. All he wanted was to touch those wrists that were sliding over his head as fingers ran through his hair. All he needed was to touch the cock that was waving in front of his lips, waiting to be swallowed and tasted.

“You will not get to come today, Mister Smith,” Mr. Novak added. “You will not touch yourself this weekend. I want you here in my office on Monday morning when you’ve had time to learn your lesson and do more research. Do you understand me, Mister Smith?”

Mr. Novak looked down at the beautifully frustrated man on his knees. Dean looked up, his long black lashes looking so pretty against his skin. Mr. Novak made a mental to note to buy some lip gloss for Dean. Meanwhile, Dean saw Mr. Novak’s blue tie hanging against his chest while his cock waited for Dean. The sight almost pained Dean because it was so perfect. Above him, like a dark angel, was the commanding face of someone not to be disobeyed, although Dean was curious to try.

“Do you understand, Mister Smith?” Mr. Novak asked once more.

“Yes, sir,” Dean answered easily, staring at the precome dripping from Mr. Novak’s cock.

“Then proceed,” Mr. Novak ordered.

Dean obeyed.

 

Sunday evening took its time arriving. Dean constantly paced his room waiting for it. At midnight, Sunday finally arrived, and Dean looked down at his flashing phone to see a text from his boss.

“1 day left,” it read. That was all.

Regardless of the rules, Dean couldn’t stop his hips from rutting upward every once in a while. He pushed into the air, against the fabric of his jeans, against the counter during breakfast or the tiles in the shower. More than anything, Dean needed to be touched, and he wanted Castiel Novak to be the one to do it.

He could vividly imagine Mr. Novak’s arms flexing, perhaps while he stripped off his jacket. He could see the glare of those blue eyes gazing down at him from above. He could practically feel the rush of air as Mr. Novak would walk by. Mr. Novak’s tie would fall to Dean’s feet, and Dean would be told to retrieve it.

Dean humped the air involuntarily. His breaths were uneven at the thought of Mr. Novak commanding him to stand on all fours, to beg for his cock like a dog for a bone.

Dean had to stop. He wasn’t allowed to touch himself. He had to stop picturing Mr. Novak’s wrists, his thighs, his calves. Dean wanted to suck on those thighs for hours. He wanted to feel Castiel as desperate as he was. Again, Dean’s body rose into the air and had to distract himself.

 

Monday morning arrived at six o’clock, beeping eagerly in Dean’s ear. Dean grumbled faintly at the sound, but only because of the instant awareness of his discomfort that came with it. He forced himself into too tight clothes after an uncomfortably quick shower. He made himself eat a piece of toast and drink his kiwi water. He then gripped his briefcase firmly and hastened down the street toward work.


	4. The Private Elevator

**Notes for the Chapter:**

> warnings: marking, dirty talk, elevator sex, tie kink, safewording/discussion about comfort in the relationship

Dean practically skipped into the office building, his briefcase swaying at his side and his tie flipped backward unknowingly by the wind. His grin went from ear to ear, however, as he stepped through the glass doors and saw Mr. Novak standing with the newspaper near his nose. When he looked up, those bright blue eyes smiled brilliantly while Mr. Novak ran his tongue over his lips and folded his paper in half.

“Ah, Mister Smith!” he said innocently. “Right on time, as usual.”

“Yes, sir,” Dean answered happily, maintaining eye contact despite the urge to inspect the details of Mr. Novak’s navy suit.

“I was hoping to be able to speak with you this morning,” Mr. Novak smiled politely. He gestured toward the elevators. “I thought we could use my own private elevator.”

“Certainly,” Dean responded with a nod, walking at Mr. Novak’s side.

The two elevators were side by side at the end of the main lobby. Mr. Novak’s private elevator was operated by his name badge alone, unlike the public elevator which ran without asking any identification. When Dean walked forward with him, Mr. Novak smirked, flashily took his badge from his wallet, and scanned it easily while watching Dean’s face. Dean, meanwhile, simply watched Mr. Novak’s jacket rise away from his wrist. Dean swallowed hard.

They stepped into the elevator together and Dean pressed the button for floor seven. Just as the elevator took off, Mr. Novak reached over again and hit a red button that was off to the side.

“Oops,” he whispered, stepping forward. The elevator had halted suddenly. “Looks like the elevator’s stuck again. You cannot rely on these old things.”

Dean pressed forward eagerly, dropped his briefcase with a thud, and spread his hands over Mr. Novak’s hips. Gently, Dean leaned forward and pressed their lips together. He sucked Mr. Novak’s bottom lip between his teeth.

“Were you a good boy this weekend?” Mr. Novak asked around Dean’s tongue.

“Yes, sir,” Dean breathed hungrily.

“Are you ready for your punishment to be over?” Mr. Novak asked tauntingly.

“Please, sir,” Dean whispered, “yes.”

Dean’s hips slotted against Mr. Novak’s, and Mr. Novak tutted. Dean whined in the back of his throat.

“Sh,” Mr. Novak whispered. He ran a hand through Dean’s hair and kissed his neck below the ear. “Not yet, Mister Smith. You have to put your briefcase away first, and then you can come in my office.”

Dean whined again, but nodded against Mr. Novak’s hand on his face.

“You’re so good for me, Mister Smith,” Mr. Novak whispered. While kissing Dean’s ear, he reached over and hit the button that made the elevator move again. “Not long now, and I’ll have you bent over so prettily for me.”

Dean inhaled deeply, closed his eyes, and nodded.

When they reached floor seven, Mr. Novak stepped back, tapped his watch, and saw Dean walk swiftly, and slightly uncomfortably, down the hall to his corner office. Dean knew Mr. Novak was only doing this to torment him, but he wanted to show that he could take it. So, hurriedly, he rushed to drop his briefcase by his desk. When he turned around, however, he’d only made it halfway down the hall again before Mr. Adler waved him over. Glancing over his shoulder, Dean saw that the elevator doors were closed.

“Mr. Smith!” Mr. Adler beamed. “Do you have a moment?”

Dean opened his mouth as if to argue, but Mr. Adler laughed and gestured for Dean to come inside. Completely oblivious to Dean’s discomfort, Mr. Adler immediately began discussing the month’s fiscal goals.

 

Dean wasn’t sure how long he’d been in Mr. Adler’s office, or how many different ways he could say that he agreed with what Mr. Adler was saying. He was siting attentively, however, keeping thoughts of his other boss free from his mind, until he heard a knock on Mr. Adler’s door.

“Mr. Adler,” Mr. Novak grinned from the doorway. “Might I trouble you for a moment?”

Dean whipped his head around so fast that he felt dizzy. Mr. Adler stood, re-buttoned his suit jacket, and nodded his head deferentially.

“Hello, Mr. Novak,” Mr. Adler smiled. “You are, of course, welcome any time! What can I do for you?”

From his seat in front of Mr. Adler’s desk, Dean turned to meet Mr. Novak’s eyes boldly washing over him. Casually, Mr. Novak turned and spoke to Mr. Adler.

“Actually, I’m in need of some assistance,” Mr. Novak spoke believably, “and I think Mister Smith here would be perfect for the job. Can I borrow him?”

Dean’s ears went pink, but he stood with practiced nonchalance.

“Of course,” Mr. Adler agreed. “We’ve just finished discussing this month’s goals, haven’t we, Mr. Smith?”

Dean nodded, said a polite, “Yes, sir,” and walked over to Mr. Novak.

“Thank you, Mr. Adler,” Mr. Novak nodded. Then he led the way to his private elevator.

The elevator door had barely closed when Dean was wrapped inside of Mr. Novak’s arms.

“I’m so sorry,” Mr. Novak whispered. His hands nimbly unbuttoned Dean’s pants as he spoke. “I thought it would be a shorter meeting with Mr. Adler.”

Dean breathed heavily against Mr. Novak’s temple, his head tilted upward. Mr. Novak kissed along his jaw and neck over and over.

“I’m so sorry,” he kept whispering.

Finally, Dean’s pants fell to the ground and his cock was in Mr. Novak’s soft palm.

“You forgot to hit stop,” Dean panicked shortly. Mr. Novak, however, blindly hit buttons on the wall until they lurched to a stop.

“You’ve been so good for me, Mister Smith,” Mr. Novak breathed. He ran his hand over Dean’s cock, rubbing around its head and shaft alternately. “You’re so good.”

“I need,” Dean gasped. His sentence was cut off by the pleasure of Mr. Novak kissing the pulse point on his neck.

“Tell me what you need,” Mr. Novak sighed against Dean. His hot breath rushed over Dean’s neck and down the collar of his shirt. “Anything.”

Dean’s fingers fumbled on Mr. Novak’s pants. Silently, he unfastened them, releasing his hard cock into the heated air between them.

“I need to touch you,” Dean begged.

Mr. Novak pushed until Dean’s back was against the wall. With one hand, he grabbed both of their cocks and started twisting his hand up and down. His other hand landed tensely beside Dean’s face against the wall. Dean immediately turned to suck on Mr. Novak’s wrist while his fingers wound around Mr. Novak’s neck.

While licking Mr. Novak’s wrist just below his shirt cuff, Dean loosened Mr. Novak’s tie, but didn’t remove it. Quickly, he unbuttoned Mr. Novak’s dress shirt and saw the navy blue tie rest against his pale chest. Dean’s hands immediately went over Mr. Novak’s nipples, resulting in several sudden, feverish kisses along Dean’s cheek and the corner of his mouth.

Breathing hotly, the both of them pushed closer together, sucking, pinching, and kissing any skin they could find.

“Please,” Dean breathed.

His hands wound into the hair on the back of Mr. Novak’s head, pulling him forward as he sucked bruises onto Dean’s neck.

“Sir,” Dean whispered, pulling Mr. Novak tighter against him.

Mr. Novak’s hand glided easily around them both, mixing their precome and spreading it around them both. Dean, who had been waiting for three days to be touched, felt himself already on the edge of coming.

“Please,” Dean begged happily.

“You don’t have to wait,” Mr. Novak purred. “You’ve waited long enough. Come, Mister Smith.”

Dean’s hips lifted upward forcing himself more and more into Mr. Novak’s grip. Then, finally, he came. He released across Mr. Novak’s chest, thankfully not getting anything on his own suit. Mr. Novak slowed his movements to help Dean enjoy his orgasm, but he kept rutting into his fist, needy and desperate. His forehead was just beginning to sweat.

“Do I do this to you?” Dean panted softly, running his hands through Mr. Novak’s hair.

Mr. Novak continued to breathe heavily and plaster kisses to Dean’s neck. Dean could feel Mr. Novak frantic for release.

“Is this is what I do to you?” Dean whispered, closing his eyes. “I wish you could have seen how I needed you this weekend. Hours of sitting with my hands white knuckling the sheets, desperate to touch myself, to pretend it was you. I wish I could show you how desperate you made me.”

Mr. Novak groaned involuntarily, so close that even Dean could feel it.

“You make me so hard,” Dean continued softly while Mr. Novak bit along his neck. “The first day I worked here, I got home and felt myself for hours trying to recreate what you did to me. I needed you so badly that night.”

Mr. Novak started to falter, his movements jerky.

“Please, sir,” Dean whispered happily. “I want to taste you again. Please. Come.”

Immediately, Mr. Novak came in bursts over their chests. Slowly, his biting stopped and Mr. Novak ran his tongue over the places he’d left marks. When Mr. Novak’s hand finally stopped, Dean simply pushed Mr. Novak’s hips until Mr. Novak was pressed against the wall. Keeping eye contact, Dean kneeled down. Slowly, he licked the length of Mr. Novak’s cock, sucking on the come he found there. Then he trailed his tongue over Mr. Novak’s stomach and sucked off the splashes of white they’d both made.

When finally Dean stood, he smirked.

“Your tie is wet,” he whispered.

While looking Mr. Novak directly in the eye, Dean pressed the fabric to his lips and sucked the tip of it.

“Dean,” Mr. Novak breathed quietly.

“You promised to have me in your office today, sir,” Dean smiled mischievously.

He let the tie drop from his lips and gazed down at it, resting against Mr. Novak’s chest. Smooth, pale, and firm, Mr. Novak’s chest rose and fell with each of his heavy breaths. Dean watched Mr. Novak’s eyes flash suspiciously, as if he knew what Dean was going to say next.

“I’m starting to think,” Dean spoke purposefully, “you don’t know how to keep your promises.”

Mr. Novak spent one second smiling gratefully before he stepped forward and away from the wall. Quickly, he moved behind Dean and grabbed his wrist. In a sudden moment, Dean found his face pressed against the wall, his arm twisted high behind his back, and his ear being breathed in hotly.

“You will show me proper respect, Mister Smith,” Mr. Novak growled roughly.

Dean smiled privately before turning his head to see blue eyes watching him challengingly. Immediately, Dean looked down.

“You will not move again until I tell you that you may. Do you understand?” Mr. Novak commanded.

Dean didn’t respond.

Mr. Novak’s lips twitched and he hoisted Dean’s arm higher behind his back, earning a gasp of surprise.

“Do you understand, Mister Smith?” he repeated darkly.

“Yes, sir,” Dean answered reluctantly. He tried to keep the smile from his voice.

Immediately, Mr. Novak backed away, released Dean’s arm, and waited to see if Dean would move. Obediently, however, Dean stood with his arm behind his back just as Mr. Novak had left it. Mr. Novak nodded, looked down, and dressed himself. When he was dressed once again, the tip of his tie slightly darker than the rest of it, Mr. Novak stepped forward to place a surprisingly gentle kiss to the back of Dean’s neck.

“You may turn around now, Mister Smith,” Mr. Novak allowed. When Dean turned, he kept his gaze down. Slowly, Mr. Novak tipped Dean’s chin upward so their eyes met. “You will have to be punished for doubting me, Mister Smith.”

Dean didn’t move. This is what he was waiting for. This is what had him most curious. He stared.

“If I make you a promise,” Mr. Novak continued, searching Dean’s eyes, “I will deliver it. Sometimes it will come in an unexpected way, but nevertheless, I will fulfill all that I promise you.”

Dean swallowed hard, looking from Mr. Novak’s serious expression back to his happy yet dark eyes.

“Now,” Mr. Novak spoke hoarsely. With a smile, he hit the button on the elevator that made it move again. Panicking, Dean looked down to see that his pants were still at his ankles. “In fifteen seconds, the elevator doors will open.”

Dean shivered, glanced at the elevator doors, and tried not to move. The tops of his ears were red with fear as he imagined businessmen from around the world seeing him exposed inside of his boss’s private elevator. He shifted his weight to a different foot nervously. He considered using his safeword so Mr. Novak would stop the elevator. Instead, however, he looked into Mr. Novak’s eyes and saw a smile.

‘Trust me,’ his eyes were saying.

Dean swallowed hard, breathing unsteadily. He felt his stomach turn as the elevator slowed to a halt. Any second now, the doors would open, as Mr. Novak had promised. Still, Mr. Novak held Dean’s chin in his hand and kept his eyes level.

‘Trust me,’ his eyes were demanding.

Dean took a deep breath through his nose, his brows furrowed with anxiety, and he waited for the doors to open.

Slowly, the doors separated and light from the office drifted inside.

“Do not look,” Mr. Novak ordered. “Look at my eyes only.”

Dean’s eyes were wide, terrified. He could be fired and humiliated. This could all be a trap of Mr. Novak’s design. Mr. Novak seemed to understand Dean’s concern, because he dropped his hand and whispered, “Do you need to safeword?”

Dean hesitated.

Mr. Novak turned and hit the button that closed the elevator doors. Now that he was private once again, Dean let out a shaky breath.

“Why didn’t you safeword?” Mr. Novak whispered, running his hands up and down Dean’s arms soothingly. “If you are this anxious, you need to safeword. That’s why we have one. Do you understand?”

“Yes, sir,” Dean answered weakly. He felt like his knees were about to give out.

Mr. Novak smiled softly.

“Dean,” he sighed. “Would you like to put your pants back on now?”

Dean nodded quickly, and Mr. Novak stepped back with a nod. Dean immediately rushed to lift up his pants and buckle his belt. He looked almost the same as when he’d first entered the elevator.

“Better?” Mr. Novak asked.

Dean nodded, but blush was creeping along his cheeks and neck.

“I’m sorry,” he whispered.

Mr. Novak shook his head, hit the button to open the doors, and grabbed Dean’s hand.

Slowly, Mr. Novak pulled Dean into the reception area. Dean looked over his shoulders and around the open rooms. No one was there.

“I sent them away for the hour,” Mr. Novak whispered, still pulling Dean toward his office.

He kept his eyes on Dean, smoothing his thumb over Dean’s hand as he walked. Dean, meanwhile, felt shaky and uncertain. His head was spinning as he came down from his anxiety, and he felt guilty. For a reason he couldn’t place, Dean felt guilty down to his soul.

Eventually, Mr. Novak opened his office door, pulled Dean inside, closed the door, and walked Dean to the most comfortable leather chair. Dean fell into the seat easily, like his legs couldn’t have held up longer anyway. Mr. Novak walked behind him for a moment and came back with a bottle of water.

“Here, Dean,” Mr. Novak offered.

Dean accepted the water bottle and looked up at Mr. Novak’s kind smile. For some reason, Dean had expected him to be angry. With a sigh, Mr. Novak sat down on the coffee table in front of Dean. Their knees bumped into each other and Mr. Novak smiled. He let Dean finish the drink he was taking before speaking.

“What happened, Dean?” he asked gently. He kept his eyes on Dean, but did not touch him.

“I was scared,” Dean answered, blushing darkly. He felt incredibly embarrassed, so he tapped his fingers on the water bottle nervously. “I thought I was going to be humiliated.”

Mr. Novak nodded, his eyes soft but serious, and he took a deep breath.

“I moved too quickly,” Mr. Novak spoke. Before Dean could argue, he clarified, “I asked you to trust me without first proving I can be trusted. I’m sorry, Dean.”

Dean frowned, unsure what to think.

“May I touch your knee, Dean?” Mr. Novak asked. “You’re shaking, and I’d like to help you calm down.”

Dean nodded. He hadn’t realized until Mr. Novak said something, but his knees were quivering uncontrollably. Gently, tenderly, Mr. Novak pressed his palms over Dean’s knees and thighs, smoothing over him and comforting him.

“It’s okay, Dean,” Mr. Novak whispered. “No one is going to hurt you. I’m not going to hurt you.”

“I wanted to trust you,” Dean whispered back. “I’m sorry.”

“Sh, Dean,” Mr. Novak answered. “It’s okay that you don’t trust me yet. I will earn your trust. It was a mistake for me to ask so much of you so soon. I’m very sorry, Dean. Our relationship is about what makes each of us most comfortable, and I pushed you too far.”

“I should have used my safeword,” Dean argued.

“Yes,” Mr. Novak smiled. He rubbed Dean’s legs gently and laughed under his breath. “It’s hard for me to know when you’re uncomfortably anxious if you don’t tell me. We need to be able to communicate. Would it help if I asked you more often which color you’re at? Green if you’re doing well, yellow if you’re hesitant, and red if you’re uncomfortable. Would that help?”

Dean’s expression softened while he considered the suggestion.

“Yes,” he answered, finally. “I’m sorry. This is difficult for me because I don’t want to disappoint you. I want to push myself to my limit, but I need to not go past it.”

Mr. Novak nodded.

“I understand completely, Dean,” he smiled. “I will ask you more often how you’re feeling to make sure we’re both on the same page. Is there anything else I can do to make you more comfortable?”

Dean bit his lip. He thought for a minute before blushing.

“It’s silly,” he whispered.

“If it helps you to feel safe and protected, it won’t be silly to me,” Mr. Novak responded.

“I want,” Dean hesitated. “I want you to kiss me before you ask me to do something.”

Mr. Novak tilted his head. His hands were still gliding over Dean’s legs, which were considerably less shaky now, and he gave Dean a confused smile.

“I mean,” Dean said, “when you told me to not look anywhere but your eyes, I was scared. I think if you’d kissed me first, I would have felt calmer. It would remind me that you do actually care if I’m comfortable, and it would help me to trust you.”

Mr. Novak looked down for a moment before nodding.

“I don’t think that’s silly at all,” Mr. Novak said quietly. “I think that’s a brilliant point, and I’m surprised I didn’t think of it.”

Dean blushed before taking a deep breath. He felt the tension leave his shoulders and he took another drink of the water bottle. When he looked back into Mr. Novak’s eyes, he saw them smile peaceably.

“You riled me up today, Mr. Smith,” Mr. Novak grinned. “You’re going to fight me every once in a while, aren’t you?”

Dean smiled and nodded.

“I’m curious to see what will happen when I do,” he shared openly with a shrug.

Mr. Novak licked his lips, stood, and looked Dean up and down.

“What do you think, Mister Smith?” he asked. “We have a half an hour before you’ll need to actually get back to work.”

Dean took a deep breath, stood, and set his water bottle down. He wrapped his hands around Mr. Novak’s waist and leaned forward for a hug. Immediately, Mr. Novak covered him with the warmth of his arms, rubbing his back slowly.

“I’d like to rest with you right now, sir,” Dean responded. “Maybe we can make out in your office a little bit before I go to work.”

“I think I can manage that,” Mr. Novak smiled, kissing Dean’s temple. “Will you come to my office again at the end of the day? I have something I’d like to give you.”

“What about my punishment?” Dean said, pulling away with shock. He added an impish, “sir.”

“If you still need it at the end of the day, I’m sure we can sort out something for you.”

Dean smiled, and Mr. Novak smiled happily back. Together, they sat on the leather sofa against the navy curtains. They spent their time holding each other, kissing each other, and talking to each other. By the end of the thirty minutes they spent together, Dean was back to taunting his boss, and Mr. Novak was pressing a gentle kiss to the base of Dean’s neck before sending him on his way.

Dean had made it all the way into the elevator by the time he realized that his neck was covered in red marks. He hit the button for the first floor, ran from the office building for a very early lunch, and bought a turtleneck sweater that rose just high enough to cover the marks. Luckily, it was still chill enough outside for him to pass innocuously in the sweater. No one batted an eye when he came back to the seventh floor wearing the sweater, and no one disturbed him once his sat down in his office with the door closed.


	5. Punishment

**Summary for the Chapter:**

> Mr. Novak gives Dean a surprising gift.

**Notes for the Chapter:**

> Kinks: lip gloss, spanking, begging, dirty talk, anal sex, really rough sex, like very hard and rough and lots of spanking (aftercare is in the next chapter)

Dean neatly folded his last sales report of the day before tucking it into the manila folder headed to the records department. He’d written a note summarizing the report and suggesting a change to the format, placed it on top of the file, and closed the folder with a sigh. Looking up at the clock caused a stirring in his stomach. With a nod to steady himself, he grabbed his suit jacket and briefcase before leaving his office.

“Off for the night, Mr. Smith?” Mr. Adler asked, raising his coffee cup in salute.

“As soon as I deliver these reports,” Dean grinned.

Mr. Adler smiled, dazed a little by the sight, and nodded his head in a soft farewell. Dean continued to the elevator, his suit jacket draped over an arm, and pressed the button for the eighth floor.

When the doors opened, Dean was greeted with the sight of the receptionist’s smile.

“Mr. Smith?” she spoke, leaning forward a bit. When Dean nodded, she smiled. “Mr. Novak is in a meeting at the moment. He asked me to have you sit in the lounge until he’s ready for you.”

“Sounds good,” Dean answered somewhat nervously. “Thank you, Meg.”

Sitting in the lounge beforehand was exactly what Dean needed. As soon as he sat in the leather armchair, he felt a shaking breath escape his lips. Although he’d been avoiding the thoughts, he’d been internally wondering what surprise Mr. Novak could possibly have prepared for him. So many suspicions had crossed his mind, but he tried to keep his hopes in check. As images of ropes and gags and plugs and riding crops flashed in his mind now, Dean didn’t realize that time was still moving. He’d just come to the image of Mr. Novak brushing the soft leather of the riding crop against his inner thighs when he heard someone say his name.

“Dean Smith,” Mr. Novak smiled from the entry to the lounge. “Sorry to keep you waiting.”

“Not at all,” Dean jumped up. He cleared his throat nervously, flicked his gaze over Mr. Novak’s shoulder to the receptionist, and tried to steady his heartrate.

“Well, then, Mister Smith,” Mr. Novak said slowly, “you can come into my office now.” As they walked by the receptionist, Mr. Novak leaned over his shoulder and said, “You can go home now, Meg. This is my last meeting of the day.”

“Thank you, sir,” she answered promptly.

She stood and rifled through a few papers before gathering her purse to leave. By the time she was in the elevator, Mr. Novak was closing the door to his office.

“You can put your clothes on the coffee table, Mister Smith,” Mr. Novak waved casually while locking the office door behind him.

While Dean unbuttoned his shirt and loosened his tie, Mr. Novak closed the navy drapes over the windows in the office to give them privacy. Dean fumbled at his belt when Mr. Novak suddenly turned around and smiled calmly at him. Mr. Novak crossed his arms, smiled, and watched as Dean blushed. Dean’s pants eventually fell to the ground, and he stood in his socks and underwear. Mr. Novak raised his eyebrow until Dean swallowed hard, tugged off his socks, and dropped his last piece of clothing onto the coffee table.

“Thank you, Mister Smith,” Mr. Novak whispered. “Would you like to see the gift I have for you?”

Dean’s eyes widened just barely, and he nodded.

“Yes, sir,” he spoke lightly.

Mr. Novak grinned, walked to his desk, and opened the bottommost drawer. Out of it, he pulled two objects. One was wrapped in a small gift bag, the size of a baseball, and the other was a small mirror with a flimsy wire stand. Mr. Novak placed the mirror on his desk, facing Dean, and carried the bag over to him.

“I thought,” Mr. Novak said deliberately gently, “that this would make you look and feel fantastic.”

Dean’s brows furrowed, but he accepted the bag curiously.

“May I open it now, sir?” he asked politely, his eyes downcast.

“Not yet,” Mr. Novak smiled. “First…”

Mr. Novak leaned forward, holding Dean’s neck in place with his palm, and gently kissed him. Dean leaned as far forward as he thought he could get away with, sucking Mr. Novak’s lips and waiting for his tongue to push against him. Instead, however, Mr. Novak sighed and stepped back. The hand that was on Dean’s neck slid up partway until Mr. Novak’s thumb was brushing over Dean’s bottom lip.

“Now you may open it, Mister Smith,” Mr. Novak hummed.

Dean looked excitedly at the pink and yellow tissue paper. With one hand, he reached down into the bag and felt something smooth and plastic and flat. His brows furrowed and he pulled the item out.

Between his forefinger and thumb was a heart shaped plastic container. Inside of it was something glittery and pink. Dean raised an eyebrow before he realized what he was holding. It was a container of lip gloss. Dean started to smile, looking up at his boss with dilated pupils.

“Would you like to put it on?” Mr. Novak asked quietly.

“Will you do it?” Dean replied softly. “I want you to do it, sir.”

Mr. Novak’s eyes beamed and he nodded. When he stepped forward, Dean moved his hand out of the way and pushed forward to place a small kiss against Mr. Novak’s lips.

“Thank you, sir,” Dean said easily. Then he took a step back, handed Mr. Novak the lip gloss, and blushed. “You can punish me for that, too, if you’d like, sir.”

“I will,” Mr. Novak promised.

Without any further words, Mr. Novak popped open the top of the heart and dipped his forefinger into the pink gloss. Looking as though he was only half concentrating, Mr. Novak placed his finger to Dean’s lips. He watched the vague glitter spread over Dean’s already pink lips. The color barely showed up against Dean, but the glitter managed to define his lips in a more direct way. As Mr. Novak brushed his fingers over Dean’s lips, Dean watched Mr. Novak’s body react. Almost immediately when the lip gloss covered his lips, Mr. Novak was clenching his fists and looking like he was ready to tear Dean to pieces.

“Please, sir,” Dean whispered. “Can I see?”

Mr. Novak tossed the lip gloss onto the coffee table, on top of Dean’s clothes. Then he reached forward, clutching Dean’s hips sharply. His fingernails dug into Dean a little bit, and he sucked in a deep breath while he felt his cock rise more eagerly. Mr. Novak said nothing for a minute. He just stared at Dean’s freckles, his eyes, his beautiful lashes, and his full pink lips. Then Mr. Novak looked down at Dean’s body and bit the inside of his cheek.

“You may see yourself,” Mr. Novak spoke hoarsely, “while you are being punished. For now, I want you to stand still.”

Dean didn’t move when Mr. Novak stepped backward and began to strip. Dean tried to breathe evenly when his boss’s tie fell to the ground, followed by his shirt, pants, and underwear. Soon, Mr. Novak was standing naked in front of Dean, his cock thick and throbbing.

“Do you remember why you are being punished today, Mister Smith?” Mr. Novak asked headily. He stepped out of his clothes and let Dean look down his body for the first time.

Dean almost couldn’t answer. Castiel Novak’s body was perfectly pale and perfectly tan, and his hip bones were the most pronounced he’d ever seen. Dean stared at those hipbones and imagined what they must look like as they thrust forward. Dean clenched his toes and swallowed hard. The hair on Mr. Novak’s thighs was lightly accenting the curves of his muscles. Mr. Novak had the legs of a runner, and all Dean wanted to do was sit between them, sucking on them for hours without end. Mr. Novak cleared his throat, catching Dean’s attention once again.

“I doubted you,” Dean answered suddenly, “and I taunted you, sir.”

“You were disrespectful,” Mr. Novak nodded in agreement. “Can you think of a way we can solve this issue for you?”

Dean licked his lips, tasting the gloss that was still wet on his lips.

“You can spank me, sir,” Dean spoke quietly. “Spanking will help me to learn.”

Dean tried and failed to stop his hips from pushing forward into the air. His cock was hot and heavy, and he needed to be bent over as soon as possible.

“Please, sir,” Dean whispered. “I want to learn to behave.”

Mr. Novak hummed, thinking to himself. After a moment, he nodded.

“Alright, Mister Smith. Walk over to my desk and bend over. Lay your chest against the wood and look into the mirror.”

Dean obeyed enthusiastically, practically tripping in the process. He bent over without hesitation and looked into the small mirror to see his pink, glittering lips grinning back at him. The mirror also barely showed Mr. Novak’s waist stepping forward.

“Now,” Mr. Novak began, “I will begin with ten slaps, five on each side. You will count them out loud for me, Mister Smith, but you will make no other noise. Do you understand?”

“Yes, sir,” Dean breathed.

“Tell me your color, first, Dean,” Mr. Novak added a little more gently.

“Neon green, sir,” Dean grinned. He heard Mr. Novak let out a breathy laugh behind him. Then, he felt the air in the room stir and the mood became serious.

Without any more warning, Mr. Novak brought his hand down against Dean’s left cheek. The slap stung, and Dean sucked air between his teeth quickly.

“One, sir,” Dean panted. Dean’s back arched slightly, raising his ass in the air to meet the next slap when it came.

On the same stinging cheek, the next slap landed with a loud, resonating ring.

“Two, sir,” Dean whispered.

His skin started to feel warm, and he looked into the mirror to see his eyes looking happily back at him. Green and focused, his eyes flickered to his glossy lips and to the hand raising behind him.

“Three, sir,” Dean breathed.

“Four, sir,” Dean spoke shortly after.

“Five, sir.”

Dean watched Mr. Novak’s face come into view behind him. Mr. Novak was leaning down and pressing a soft kiss to the red, stinging flesh.

“Good boy, Mister Smith,” Mr. Novak said proudly. He rubbed a hand over Dean’s ass and then turned to stand on the other side. “What’s your color now, Dean?”

“Green, sir,” Dean smiled.

Mr. Novak’s hand fell flat and firm against Dean’s right cheek.

“Six, sir,” Dean said. He pushed forward without meaning to, rubbing his cock against Mr. Novak’s desk. He held his breath to keep from moaning.

“Seven, sir,” Dean whined with the next sting. Mr. Novak’s hand had landed and then grabbed Dean’s flesh hard, squeezing his ass. Dean closed his eyes tightly and sighed.

“Eight, sir,” Dean said. His voice sounded needy and desperate, and his ass lifted into the air for the next slap.

“Nine, sir!” Dean moaned when the next hit landed.

“Ten, sir!”

Mr. Novak immediately leaned down to kiss Dean’s ass.

“Is that enough for you right now, Mister Smith?” Mr. Novak asked darkly.

“Please, sir,” Dean panted. “Please.”

“We must be clearer when we speak, Mister Smith,” Mr. Novak reprimanded. “Use complete sentences, please.”

“Please, sir,” Dean breathed. “Give me more!”

Mr. Novak raised an eyebrow and looked at Dean’s reflection in the mirror.

“Stand up, Mister Smith.”

Dean stood, enjoying the heat of his ass and the throb of his cock. He waited.

“Put your hands on your ass, Mister Smith.”

Dean reached slowly behind him, rubbing his hands over his warm cheeks. He heard a sigh from behind him. When he looked into the mirror, he saw Mr. Novak’s cock in his hand. He was rubbing it slowly while watching Dean squeeze his own ass.

“I want you to stretch yourself out for me, Mister Smith,” Mr. Novak spoke hoarsely. “Finger yourself. There is lube in the box beside my monitor.”

Dean looked at the monitor on the side of Mr. Novak’s desk and reached over for the box. Inside, as promised, was a bottle of lube. Dean couldn’t help but picture Mr. Novak, alone in his office, properly dressed except for his pants at his ankles and his hand rubbing over his hard, wet cock over and over. Dean shivered at the thought, wondering if he thought of Dean when he touched himself.

“Finger yourself, Mister Smith,” Mr. Novak commanded. “I want to see your fingers working in and out of you, stretching you open for my cock.”

“Ah!” Dean gasped quietly. He opened the bottle easily and squeezed the cold lube onto his fingers. Almost too quickly, he reached behind himself and pushed a finger inside. “Oh!”

Mr. Novak’s reflection moved faster over his cock.

“That’s right, Mister Smith,” he praised gently. “You’ve got to get ready to be filled. Do you want my cock today, Mister Smith?”

“Yes, sir,” Dean breathed, pushing back onto his finger. He started adding the second one before he was ready. “Ah!” he gasped at the burn. Still, he pushed into himself, desperate to have his boss inside of him.

“You’re doing well, Mister Smith,” Mr. Novak said easily. He watched Dean working himself while his glossy, pink lips spread wide for his gasps. “You’re going to have to start wearing a plug for me, Mister Smith.”

“Please, sir,” Dean whined quietly.

“Tell me when you’re ready, Dean,” Mr. Novak whispered. He leaned down, kissed Dean’s ear, and whispered, “I’m going to fuck you so hard, you’ll have trouble sitting during the meeting next Monday.”

Dean’s breathing accelerated and his heart rate increased. He pushed a third finger into himself and shook his head.

“Please, sir,” he begged. “Do me now.”

“Are you properly prepared?” Mr. Novak asked roughly.

“I don’t care, sir,” Dean begged. “Please. I need you now, sir.”

“You need to be ready, Mister Smith,” Mr. Novak answered firmly. “Are you ready?”

Dean hesitated while he moved his fingers in a scissoring motion to loosen his hole. A few seconds later, he nodded.

“Please, sir,” he begged. “I need your cock now. I’ve needed your cock for days, sir. Please! I’ve been dreaming of your cock stuffed inside of me, filling me so much that I feel it for days. Please, sir!”

Mr. Novak growled in the back of his throat and shoved Dean down onto the desk again. Dean’s nipples were hard against the cool wood, and he deliberately rubbed them over the desk while Mr. Novak lined himself up behind him. Dean raised his ass a little bit into the air to help Mr. Novak, who was rubbing his cock all over Dean’s ass territorially.

“Do you feel that, Mister Smith?” Mr. Novak growled deeply. “Do you feel how hard my cock is right now?”

“Please, sir!” Dean begged. He pressed his ass backwards, arching his back.

“Ah,” Mr. Novak sighed, pressing the head of his cock against the warmth of Dean’s hole.

Mr. Novak grabbed Dean’s hips hard and pushed him forward. Dean’s arms flung out ahead of him, grabbing the opposite edge of the desk as he stared at his pink lips quivering in the mirror. Mr. Novak’s fingernails dug into Dean’s ass and finally, finally!, Dean felt Mr. Novak pushing inside. In the mirror, Dean saw those sharp hipbones rut forward slowly, pushing little by little.

“Fuck me, sir,” Dean begged. He moaned quietly. “Please!”

Mr. Novak was halfway inside of Dean when he paused and slapped Dean’s hip.

“Ah!” Dean panted.

“I told you to be quiet, Mister Smith,” he growled.

Another slap landed against Dean, who immediately muttered, “Fuck!”

A third slap stung his skin as Mr. Novak’s cock continued to dig into Dean’s ass.

“Be silent, Mister Smith,” Mr. Novak warned, “or you won’t get to come today.”

Dean stifled a whine and closed his eyes tightly. In the mirror, Mr. Novak could see Dean’s glittery, pink lips shake.

“What’s your color, Dean?” Mr. Novak asked cautiously.

“Green,” Dean whispered. “Green, sir.”

Mr. Novak nodded and pushed forward, stepping close until he was buried balls deep in Dean’s ass. Dutifully, however, Dean made no sound. Mr. Novak smoothed a hand over Dean’s back and nodded.

“Good boy, Dean,” he grumbled darkly. “You’re going to let me do whatever I want to you, aren’t you?”

Dean nodded, his eyes still scrunched closed. Mr. Novak leaned down and kissed Dean’s shoulder blade.

“I’m going to fuck you now, Mister Smith,” Mr. Novak explained. “Do you remember your safeword?”

“Yes, sir,” Dean answered quietly.

“Say it now for me,” Mr. Novak said. His cock was throbbing inside of Dean, and Dean whimpered pitifully.

“Impala,” he said breathily. “Please, sir.”

“Use the safeword if you need to, Dean,” Mr. Novak instructed seriously. “Are you ready?”

“Yes, sir,” Dean answered, enjoying the feeling of Mr. Novak’s hands running over his spine. “Please, sir.”

Immediately, Mr. Novak pulled almost entirely out of Dean before thrusting forward so hard that the whole desk shook. The pencils and pens rattled in their organizers to Dean’s right, and the monitor wiggled a little bit to his left. Again, Mr. Novak pulled out most of the way before rushing back in. Slowly, deliberately, he continued the hard thrusts for a few agonizing minutes.

Dean felt himself stretching, burning, breaking around his boss’s cock. All he could think was, ‘More, more, more!’ Luckily, Mr. Novak seemed to understand. Suddenly, his thrusts were shallower and quicker.

“I remember you loved this spot when I fucked you with my tongue,” Mr. Novak breathed quietly as he angled his next thrust.

Predictably, Dean’s back arched and he rocked the desk so hard that the pencils knocked over.

A sudden slap landed against Dean’s hip.

“Do not make a mess, Mister Smith,” Mr. Novak growled.

Dean breathed quickly, shallowly, trying his hardest not to make a sound.

Another sharp thrust knocked over the container of pens on the desk. Right after, another slap landed on his hip.

“Fuck,” Dean whispered. He didn’t think Mr. Novak had heard it at first, but then he felt Mr. Novak push forward quickly, strongly, while slapping Dean’s thigh.

“You’re disobeying me, Mister Smith,” Mr. Novak thundered. “I cannot tolerate this.”

“Spank me,” Dean begged. “I can learn if you spank me.”

Mr. Novak thrust forward shakily.

“Count them,” he growled.

“One, sir!” Dean panted.

Mr. Novak alternated between plowing forward, hitting Dean’s prostate every time, and slapping Dean’s soft hip and thigh.

“Five, sir!” Dean begged, tears in his eyes.

“What’s your color, Dean?” Mr. Novak paused, watching the tears fall from the corners of Dean’s eyes.

Dean smiled, “Green, sir. Couldn’t be greener.”

Mr. Novak reached up for Dean’s mouth, hooking his fingers inside of those painted lips. His other hand grabbed onto Dean’s hair.

“Bite if it’s too much,” Mr. Novak demanded.

They were both covered in sweat, and now Mr. Novak was setting a punishing pace with his thrusts. He shoved Dean forward, allowing Dean to suck and nibble his fingers, breathing heavily against him.

“You’re so good for me, Dean,” Mr. Novak breathed. He pushed faster and faster. “You’re so perfect.”

Dean moaned around Mr. Novak’s hand and breathed heavily. Mr. Novak pulled against Dean’s cheek and against his hair.

“Yes,” Mr. Novak breathed. He pushed forward jerkily. “Yes, Dean!”

Dean moaned and sucked Mr. Novak’s fingers.

“So perfect!” Mr. Novak panted. “I’m going to come so hard, you’ll feel me in you for days.”

Dean closed his glossy lips around Mr. Novak’s fingers, sucking them deeper and deeper as warmth spread to his stomach. He was close, too.

Mr. Novak pushed Dean forward so hard, his monitor nearly fell. Luckily, Dean reached out to stop it just in time. Finally, Mr. Novak pressed as deeply as he could inside of Dean and let himself groan.

“Yes, Dean,” he panted. “Fuck!”

Mr. Novak came, spilling hotly into Dean and ramming into him a few more times. Dean sucked on Mr. Novak’s fingers heatedly, feeling his boss shoving as far into his ass as he could. Slowly, still pressed deeply into him, Mr. Novak leaned forward across Dean’s back. He let go of Dean’s hair and reached down to his straining cock.

“Come, Dean,” he commanded.

Without delay, Dean released into Mr. Novak’s hand. Mr. Novak pumped Dean several times until Dean stopped sucking on his fingers. Together they panted, sticking to each other.

“You’re so perfect, Dean,” Mr. Novak chanted, letting his cock rest inside of Dean for a minute longer. “So perfect for me, Dean.”


	6. Windows

**Summary for the Chapter:**

> Dean is called by his boss to work on a Saturday.

**Notes for the Chapter:**

> the kinks: window sex?, exhibitionism, voyeurism, masturbation kink?, comeplay, dirty talk, praise, rough treatment, quiet sex, semi-public sex... ummm... what else?

Dean was resting on the couch in Mr. Novak’s office. Fully naked and peaceful, Dean closed his eyes and waited for Cas to dress himself.

With his pants on and his shirt left untucked, Cas knelt beside the couch.

“Thank you, Dean,” he breathed against Dean’s chin. He placed one small kiss there and then moved to his ears. “You were so good.”

“Cas,” Dean sighed. He carded a hand through his boss’s hair and shivered from a sudden chill.

“You’re amazing, Dean,” Cas smiled, quickly draping his suit jacket over Dean’s chest. “Do you want to get dressed now?”

Eyes closed, head nuzzling against Cas’s hand, and hands over his abdomen, Dean made a murmur of denial. Cas smiled crookedly, leaned forward until his head was resting on Dean’s, and closed his eyes.

“Okay,” he whispered.

 

By late morning on Saturday, Dean could sit down without feeling what Cas had done to him. Though his body was likely relieved at the fact, his heart missed the reminder. Luckily, he had a small container of lip gloss in his pocket that he could dip into whenever he needed to. When he was just sitting down after lunch, he heard his phone ring.

“Hello?” he answered absently.

“Hello, Mister Smith,” the voice clearly answered. Mr. Novak’s smile was as apparent as always, and Dean immediately sat upright. “I’m wondering if you can come to work today. I understand it’s short notice, but we’re swamped, and I’d like your help catching up. Can you spare your time this afternoon?”

Dean opened his mouth, said nothing, and wondered naively whether Cas actually needed him to work.

“If you’d like to assist me, you would be welcome to work in my office alongside me, of course.”

Dean understood the answer and smiled. “I think I can make it. I’ll need a few minutes, of course.”

“Thank you, Mister Smith. I’ll be in my office when you’re ready.”

After a knowing laugh, Dean and Cas hung up their phones. Dean immediately ran to the bathroom to take a fast shower. When he dressed, he wore a deep navy suit and a black tie. He combed his hair neatly, applied some cologne, and checked his teeth in the mirror.

 

When he arrived at Sandover, Dean was surprised to see that there actually were some people working over this particular weekend. A guard on the main floor nodded to Dean and let him pass without needing to see his identification card.

The elevator ride was painfully slow, but at least Dean had that time to compose himself. Instead of shaking with anticipation when he reached the top floor, he was steady on his feet.

“No secretary,” he whispered under his breath.

He continued walking toward Cas’s office.

“Excuse me, sir?” a woman called from the other side of the room. “Do you have a meeting with Mr. Novak today?”

Dean looked over to see the secretary peeking out from a door to the lounge, where she was probably enjoying a lunch break.

“Yes, ma’am,” Dean answered, stopping to show his identification card across the hallway. “I’m Dean Smith – Mr. Novak asked me to meet him in his office to help him complete some work.”

“Oh!” nodded the woman. “Of course! I remember him mentioning that. Sorry about that! He should be in there now, sir. Thank you!”

“Thank you,” Dean nodded with a smile.

In a few measured steps, he was at the door. The navy curtains in the office were closed, so he could see nothing inside. He knocked, swallowing hard.

“Come in,” came the heavy, deep voice of his boss. “Shut the door behind you.”

Dean obediently entered, turned, closed the door, and returned his gaze to the figure in front of him. Cas stood in front of the window, entirely naked, holding only a belt in his hands, which he quickly put on top of his desk.

“Come to the window and look at our view.”

With one hand in his pants pocket and the other clenched at his side, Dean stepped forward. When he reached the window, he stared at the cars passing by, the people scurrying about their day, the buildings all around lacking the firm presence that Sandover held. More than all of that, however, Dean saw the reflection of his boss’s cock in the window. It was half hard.

“Come here,” Mr. Novak said simply, reaching out to curl his fingers around Dean’s collar. Nimbly loosening the tie while pulling Dean close, Mr. Novak breathed deeply. “We have to be quiet today, Mister Smith. My secretary is working diligently past that door, and we mustn’t disturb her. First, though…”

Dean’s tie dropped to the floor in a puddle right when Mr. Novak leaned forward and pressed their lips together. They alternated sucking each other’s bottom lip, hot breath clashing in between them as their heads tilted. Dean had not been given permission to touch his boss, so he could only run his tongue over his lips and wait for the moment he could use those muscular thighs as ear warmers.

“Kneel for me, Mister Smith,” Mister Novak breathed hotly.

As Dean lowered himself to his knees, the phone on his boss’s desk vibrated. Mr. Novak reached over effortlessly, not having to move away from the man in front of him, and he put the phone speaker on.

“Yes, Meg?” Cas answered. While speaking, he smirked down at Dean and ran his hands through Dean’s hair. His eyes flicked from the wet, rosy lips beneath him and his own half hard cock. He nodded pointedly at Dean, giving silent instructions, even as he said over the speaker, “What is it?”

“Well,” Mr. Novak’s secretary answered. In the second it took her to continue speaking, Dean’s mouth was open on his boss’s cock while Mr. Novak was petting Dean’s head just around the ears and the back of his neck. “There’s a call coming through from the network provider and he says you specifically asked to speak with him today.”

Mister Novak smiled mischievously.

“Ah, yes,” he said smoothly. “Can you tell him to hold for one moment while I get situated?”

Dean’s pretty green eyes looked up Mister Novak’s smooth, sculpted chest.

“Of course, sir,” Meg answered. “You can pick up line one-oh-seven when you’re ready.”

“Thank you,” Mister Novak said, reaching over to turn off the phone once more. Then he lowered his voice and spoke in the rough, low way that made Dean go rigid with want. “Here’s what we’re going to do, Mister Smith.”

His mouth wrapped around Mr. Novak’s cock, Dean watched as his boss played with his hair affectionately.

“I want you to hold me, just like you are now, for the duration of this telephone call. Since your mouth will be full, you will need to tap the back of my leg three times rapidly if you need to stop. Tap my leg once if you understand.”

Trying not to give himself away, Dean lowered his eyes and stroked the back of Mr. Novak’s leg with his fingers. The cock in his mouth throbbed for a moment.

“No, Mister Smith,” Mr. Novak reacted. “You will not do that again, or I will use your tie to keep your hands behind your back. Do you understand? Tap my leg once if you understand.”

Busted, Dean gave a resigned tap to the back of Mr. Novak’s leg.

“You’re not warming my cock, Mister Smith,” he continued. “You are allowed to suck on me, to lick me, or to do whatever else you like with your mouth as long as you do not ever take me out of your mouth. Do you understand? Tap my leg again.”

Dean obeyed.

“Good boy, Mister Smith.”

Mr. Novak leaned over and clicked on the waiting line to come onto the speaker without any further conversation. Dean shifted his weight on his knees and experimentally licked Mister Novak’s cock while keeping his mouth completely over it, covering halfway down the shaft.

“This is Mr. Novak from Sandover,” Mr. Novak answered the phone professionally. He spoke as if there wasn’t a man on his knees doing everything he could with his tongue to make him blush. “Is this the Information Technology Office in New Orleans?”

The voice on the other side of the line confirmed and began to discuss the gathered data for the past month’s computer network usage.

Dean’s mouth watered around Mr. Novak’s cock, and he instinctively tried to suck the saliva back into his mouth, sucking his boss in the process. Mister Novak’s body tensed, and those strong thighs of his flexed beautifully. Dean could stare at the muscles of those thighs for hours. He raised his hand to touch them before remembering that he was not allowed to do so.

‘He can’t punish me while on the phone,’ Dean argued with himself, sucking on the cock in his mouth until it was thick, throbbing, and hard against his tongue.

Experimentally, Dean briefly ran a hand over Mr. Novak’s thigh, making it seem like an accident.

“I understand that,” Mr. Novak continued to speak over the phone, “but you have to understand that there are certain programs we need to add to the tracking list. I’d like to know if certain programs are essential. If no one is utilizing them, I’d rather save the money and lose those programs.”

Seeing that his boss was undisturbed by the error, Dean tried slowly dragging his fingers over the thighs again. This, too, could have been an accident, and Mr. Novak didn’t seem to notice. Brazenly, Dean swirled his tongue around the shaft in his mouth before reaching in front of him to knead the thighs he’d been dreaming to have to himself.

Although Dean was clearly disobeying orders, Mr. Novak didn’t seem to care. He was reaching over to write down a note from the call as if nothing was happening.

With even more gall, Dean slid one hand back and grabbed his boss’s firm ass.

“I believe so,” Mr. Novak nodded, finally finished scribbling on the paper in front of him. “Can you read me the estimate for that as well?”

Dean had supposed that the note was relevant to the network conversation he was having over the phone, but all of the sudden, there were words on a bright green paper in front of Dean’s eyes. They obstructed the view and Dean was forced to read.

‘Give me your tie from the floor and then put your hands up,’ the note read. ‘NOW.’

Dean’s cock was hard in his pants, and now he just smiled and raised an eyebrow. He looked up to see Mister Novak gazing down. Their eyes met and a challenge was issued by each of them.

Dean reached down to retrieve the tie from the floor, but instead of handing it over to his boss, he ran the silky fabric over Mister Novak’s ass. Feeling victorious, Dean enjoyed the flash in Mr. Novak’s eyes.

“Can you mail me the report?”

Mister Novak did nothing, but he stared at Dean with fiery eyes. His expression was one of triumph.

“Thank you,” he said to the speaker. “I look forward to hearing back from you again soon.”

The call ended. Suddenly less daring, Dean dropped his hands to his sides and stilled his mouth.

Mr. Novak did nothing for a moment, and Dean tried to look away, but his eyes were locked on those icy blue eyes burning into him.

“You will stand,” Mister Novak whispered darkly. “You will step back, and you will stand.”

Dean’s jaw tensed. There was no room for discussion or negotiation. All of his boldness drained away and he slid back and stood without argument. Mister Novak leaned forward, pulled the tie from Dean’s anxious hands, and set it on his desk.

Without another word, Mister Novak shoved Dean against the glass window. His back was pressed against the cool glass and he was out of breath from the sudden attack. Before he could focus, Mister Novak’s hand was at his throat, not constricting, but threatening.

“What were my instructions, Mister Smith?” he asked, his voice low and his breath hot over Dean’s face.

With Mister Novak’s thumb stroking his Adam’s apple, Dean answered quietly.

“Keep my mouth on you,” he said, “but not touch you, sir.”

“You were very bad,” Mr. Novak growled, pausing the caress of Dean’s throat.

“Are you going to spank me, sir?” Dean asked, unable to hide his eagerness.

Mr. Novak shook his head.

“You’re going to come.”

Dean waited to hear the punishment explained. Instead of hearing clarification, however, all he could hear was the sound of his boss quickly moving his hands over Dean’s chest and waist, stripping him as easily as blinking. Within seconds, Dean was standing in front of the window entirely naked.

“Anyone could see you,” Mr. Novak taunted. “There are hundreds of people crossing the street, Mister Smith, and any of them could look up here and see your cock, leaking against my window. They would know that you’re fucking your boss – or rather, that he’s fucking you.”

Dean swallowed hard but remained still. His cock was red and stiff.

“Put your hands behind your head, Mister Smith.”

Dean hesitated, uncertain about what the catch was to this punishment.

“Mister Smith, what’s your color?”

While lifting his hands above and then behind his head, he took a deep breath.

“Green, sir.”

Mr. Novak leaned forward and kissed Dean. While his mouth invaded Dean’s mouth, his hands worked to fasten the tie around Dean’s wrists to lock them together.

When he finished tying Dean’s hands together behind his head, Mr. Novak turned Dean so he was looking out of the window, his cock pressed against the cool glass.

“You will come by rubbing yourself on the window.”

Dean’s eyes widened. This was the clarification he’d been waiting for. This sounded more like a punishment.

“Don’t worry, Mister Smith. I’ll lubricate the window for you.”

Mister Novak stood in front of the window, stared at Dean’s ass, and pulled his cock over and over, moaning obscenely all the while. Finally, he came, splashing the window with his come where Dean would be rubbing.

“I should also mention,” he added, “that I will be on the phone with Mr. Adler the entire time. If you do not come by the end of the call, you will not be allowed to come for a week. If you make a noise that Mr. Adler is able to hear, you will not come for two days. Do you understand, Mister Smith?”

Dean gulped audibly.

“Yes, sir,” Dean answered.

“Before you begin,” Mr. Novak smiled, dressing himself as he spoke, “I want you to tell me why you are being punished.”

“I was bad, sir,” Dean answered immediately. “I touched you when I was told not to, sir.”

“Exactly. In response to your disobedience, you will not get to touch me or watch me for the next half hour. You will come without my help, and you will learn to cherish the times you are allowed to feel the heat of my body. Do you understand, Mister Smith?”

Dean’s mouth fell open. He was facing the window, unable to see his boss any longer. All he could sense was that Mr. Novak was sitting in his chair, directly behind Dean, probably staring at his ass while he picked up the phone receiver.

“Yes, sir,” Dean whispered, pressing the tip of his swollen dick against Mister Novak’s come on the window.

“Begin, then,” Mister Novak said. Then, into the phone, he said, “Meg, could you connect me to Mister Adler, please?”

The first three minutes were a torment for Dean. For Mr. Novak, they weren’t particularly easy either. At one point, his voice broke while he was talking because of how hot Dean was making him. Dean thrusted against the window over and over, his ass clenching and releasing and defining his beautiful muscles and hairy thighs. From behind, Mr. Novak could admire every inch of Dean’s perfect body working hard as he held back moans. On the other side, Mr. Novak knew that Dean was pounding against his come, rubbing his flushed cock in the white seed he’d left for him. As he spoke on the phone, Mr. Novak’s cock was hardening once more.

Dean, meanwhile, began to sweat. His cock was rock hard against the window, and he wasn’t entirely convinced that ramming against it as hard as he was wouldn’t break the glass. Desperate, though, he rutted against the window, feeling the warm, hot come that his boss had left for him spread all over his own cock.

“Ngh,” Dean whined quietly. He tried to contain it, but he realized then that his only hope was to be quiet enough that Mr. Adler wouldn’t hear over the phone.

Suddenly, he heard the soft sound of a zipper being pulled down. Unable to see, Dean could only guess what Mr. Novak was doing to himself.

“Ah!” Dean gasped, pushing harder against the window.

Mr. Novak hummed, which would have sounded contemplative if Dean didn’t know that he was probably stroking himself at that very moment. Hearing the sound brought Dean close, but he couldn’t come. He was reaching for his orgasm, but the now warm window, fogged up with his heavy breaths, wasn’t giving Dean enough pressure. He needed more.

“Please,” he whimpered softly. He only barely managed to keep his voice low enough that Mr. Adler wouldn’t hear. “Fuck me, please.”

“We definitely should consider resetting the program,” Mr. Novak said over the phone. Then, slightly louder, he added, “When something is bad, it needs to learn how to be better.”

“Ah,” Dean breathed against the window. He pressed again and again, trying to make himself come. His arms ached from being tied behind his head. His forehead was covered with a sheen of sweat. He panted, pushing harder and harder against the glass.

“Thank you, Mister Adler,” Mister Novak said, warning Dean that his time was almost up.

“Touch me,” Dean whispered. “Please!”

Mr. Novak tilted his head before standing. The cord to the phone stretched enough that he could stand directly behind Dean. His cock was out and dripping, ready to come. He gave it a few more tugs.

“I did say that the program should be ended, and I will always stick to my word,” Mr. Novak said over the phone, “but I do have some mercy. We’ll give it one more chance.”

There was a soft sigh when Dean felt more come land on his ass. Mister Novak wasn’t touching Dean, as he’d said he wouldn’t, but he was giving Dean just enough of a push to send him over the edge.

Immediately, Dean came. He whined loudly, unable to keep in his relief and surprise that he was coming, hard, from rutting against a window. Luckily, Mr. Novak was able to cough to cover up the sound.

“Alright, I’ll speak with you about it again later, Mr. Adler,” Mr. Novak concluded. “Sorry about the late lunch break today! I hope you go somewhere nice.”

When the receiver was replaced on Mr. Novak’s desk, Dean was panting and wobbling, ready to fall down.

“Good boy,” Mister Novak said, rushing over to hold Dean. He untied the tie with a fluid motion and helped Dean to sit in his chair. “So good, Dean. You were so good. You took your punishment very well. I’m so proud of you, Dean.”

Dean breathed heavily. His eyes shifted out of focus for a moment. After a few deep breaths, he was able to look at the window and see the white smears across it – clear evidence of what had been done.

“Oh my god,” Dean whispered.

“You did it, Dean,” Mr. Novak nodded insistently, rubbing his hands strongly up and down Dean’s thighs as he sat down. “You did it, and you were amazing.”

“Wow,” Dean said, still looking a mixture of afraid, proud, anxious, and blissful.

“Good boy, Dean,” Mr. Novak said, kissing Dean’s knees. “Good boy.”

Slowly, Dean was able to bring his focus back to where he was, and he looked forward at Cas’s happy blue eyes.

“Cas,” he breathed, unable to say anything else.

“You did it,” Cas grinned. “How do you feel?”

“That was,” Dean started. He stopped for a moment.

“You’re a glutton for punishments, aren’t you, Dean?” Cas smirked.

Dean nodded simply, and said without warning, “Kiss me?”

Cas nodded. They kissed lightly and lazily for the next forty-three minutes, before Meg called again to say that there was another call waiting.

“I’ll pick it up in one minute, thank you,” Cas smiled. Then he turned off the speaker and said to Dean, “Will you sit on my lap while I take this call?”

Dean nodded, standing to switch spots with Cas. After Cas sat down, Dean straddled him tiredly, wrapping his arms around Cas’s neck and resting his forehead on his shoulder.

“Comfy, honeybee?”

Dean laughed breathily at the endearment and nodded against Cas’s shoulder.

“Go ahead, angel,” he whispered.

Cas smiled, turned on the speaker, and trailed his fingers along Dean’s spine as he answered the waiting call.


	7. Respect

**Summary for the Chapter:**

> It's time Dean learned how to properly respect Castiel.

**Notes for the Chapter:**

> what to expect: vibrating plug (because why not) (during a meeting, too!), fluff, relationship discussion, kinda angsty pining beginning? This is more of a story chapter than a sex chapter, but there's enough to keep it interesting. :)

“Dean,” Cas smiled gently. “Wake up, bee.”

Dean’s eyes opened very slowly. Cas watched as the sleep faded from his green eyes, replaced with confusion and embarrassment. Cas laughed under his breath and ran a hand through Dean’s hair. That’s when Dean’s skin rose from the chill of the room.

“I’m naked,” he stated, his voice catching a little bit with sleep. He cleared his throat. “I fell asleep.”

Cas nodded, running his hands through Dean’s hair soothingly. Gently he moved his head and kissed Dean’s cheek.

“You fell asleep halfway through my call,” Cas said with the amusement clear in his voice. “It’s been about two hours, and I’m surprised that my typing didn’t bother you at all. It was a little difficult to reach the keys around you, though.”

Dean blushed, but Cas just kissed his other cheek affectionately.

“You could have woken me,” Dean said, deliberately casually.

“You were snoring,” Cas actually laughed. “Besides, it was comfortable for me, too. When it comes down to it, people are a lot like any other animal, you know.”

Dean shook his head at the awkwardly random statement, blushing still.

“They don’t often fall asleep on you unless they really trust you,” Cas explained. “Thank you for trusting me. I’ve become very fond of you, Dean Smith.”

Dean grinned, unable to contain the happiness of hearing those words. Then he remembered how cold he was and he whined a little in his throat, knowing he would have to move.

“Well,” Cas smiled with finality. “We should probably clean you up before you get dressed, huh?”

Dean looked at him curiously before he remembered. There was dried come on his back, his thighs, and his cock. Some of it was sticking to Cas’s nice pants as well. Dean looked around the room, relieved to see that there was a private bathroom on the side of the room. He sighed deeply, put his hands on Cas’s shoulders for support, and started to move away from his boss’s lap.

“There’s a shower in there,” Cas said simply when Dean dismounted. Dean looked up at him with surprise. “Just so you know.”

“Can I use it,” Dean asked, quietly tacking the magic word onto the end of the question, “sir?”

Cas tilted his head, looked down at his come stained pants, and bit his lip.

“Mister Smith,” Mr. Novak said, “I’m sure you’re aware that you made a noise earlier that Mr. Adler could have heard. Do you remember what I told you would happen if he heard you?”

Dean nodded, saying somewhat triumphantly, “Yes, sir. Did he hear me, sir?”

Mr. Novak raised both of his eyebrows and huffed. Dean watched his face deliberate, deciding if Dean had wormed his way out of the punishment he’d been promised if Mr. Adler heard him over the phone. Eventually, Mr. Novak stood, looked Dean up and down, and shook his head.

“He did not,” Mr. Novak answered. “You have me to thank for that, by the way.”

“I do thank you, sir,” Dean answered promptly. “I’d like to thank you even more, sir, if I can.”

Mr. Novak shook his head, smiling.

“You just sassed me, Mister Smith,” Mr. Novak said, gazing at Dean pointedly. His eyes darkened. “I think you need to learn a little more respect.”

Dean looked at the ground sadly, thwarted.

“You may use my shower, Mister Smith,” Mr. Novak said, leading the way to the private bathroom, “and once you are clean, you will wear a plug. You will wear the plug all night tonight and all day tomorrow and Monday. You may remove it when you need to take care of business, but you must replace it afterward.”

Dean nodded, opened his mouth, and then closed it again.

“We have a meeting on Monday, Mister Smith,” Mr. Novak reminded him. “I want to know that you’re ready for me whenever I want you. I want to know that I could shove you, face down, on that long conference table, in front of everyone, strip you down to your ankles, and then fuck you while you whimper beneath me.”

Mr. Novak looked down at Dean’s cock to see if Dean fully understood him. Judging by the way Dean’s cock was raised curiously, he knew Dean heard the message. Mr. Novak smirked.

“There is already a plug in the bathroom for you, Mister Smith,” Mr. Novak said, matter-of-fact. Then he nodded at Dean’s body. “You can take care of that in the shower as well. I want you to do it slowly, while I change into a different suit. You’ll leave the shower door open so I can see you perfectly. Do you understand, Mister Smith?”

“Yes, sir,” Dean said.

“Any questions?”

“No, sir.”

 

 

Monday. The first day of the work week. The day many people dread. Dean, however, awoke on Monday feeling incredibly excited. He wondered if after the meeting, Cas might actually shove his head down onto the table and fuck him roughly just because he could. He wondered if Cas would close the blinds to the room and shove him against the whiteboard on the left wall, bruising him with every harsh thrust against the wall. Dean shivered with hope.

He got ready in record time that morning, chasing down his whole grain bagel with a spinach and kiwi energy smoothie seconds before he left his apartment. He rushed to work, hoping to be the first person in the conference room, to show his boss how eager he was to prove himself. Cas had said that he needed to learn respect. Dean wondered what might happen. He hoped it involved bruising of some kind.

When he arrived at Sandover, however, Dean was immediately greeted by Mr. Adler.

“Mr. Smith!” Mr. Adler waved cheerfully. “This is your first meeting with us, isn’t it? Are you excited?”

“Extremely,” Dean answered with an award winning grin. “I’ve only ever walked by the conference room, so I’m excited to see what it feels like to be in there.”

“Well, I can tell you one thing for sure,” Mr. Adler laughed. “The table in there is the perfect height!”

Dean’s eyes went slightly wider while he tried to hide his laugh with a cough.

“When we take notes during the meetings,” Mr. Adler continued obliviously, “the paper is the perfect distance. I love that conference room table. And it’s so large!”

Mr. Adler boasted about the conference room table for the entire walk to the elevator, and Dean could only nod along and try to hide his grins. There was no way he could ever explain why the topic was so amusing to him.

Instead of riding the elevator to floor seven, they went directly to floor eight. The conferences were held in the very beginning of the work day so that the resolutions devised at the meeting could be applied immediately afterward. Dean, as a new subordinate to both the marketing and statistical analysis departments, was not expected to speak much during the meeting, so he had cleverly devised a plan to make himself irresistible to Mr. Novak after the meeting. One way or another, he was determined to be fucked in that room.

Out of the elevator, Mr. Adler and Dean walked to the right of the secretary’s desk and then past the lounge. The conference room was next, with the blinds raised so that the entire room was open. There were several people inside already, but Mr. Novak was not among them. Dean glanced quickly at Mr. Novak’s office on the opposite side of the hall in the far corner. The navy drapes were open this time, and the office looked bright and inviting, though he was not inside of that room either.

“Here we are,” Mr. Adler said, opening the door for Dean. “Home sweet home, for the next hour or so, anyway.”

Dean grinned, thanked Mr. Adler, and walked into the room. He found a chair quickly, shook hands with the people who had already settled down in the room, and then sat. He almost jumped back up again. The chairs in the room were surprisingly hard and sturdy, and he’d sat in such a way that the plug he was wearing shifted slightly. Dean moved his hips inconspicuously, trying to get the plug to settle easily. When he did, he just hoped he wouldn’t have to stand up again during the meeting.

Several minutes passed before all twenty-four people were in the room and ready. Mr. Novak was the only one missing from the group.

“Must be running late,” Mr. Adler shrugged. He turned to Dean and whispered, “It doesn’t happen often, but sometimes his elevator actually gets stuck and stops for a bit. No one knows why.”

Dean nodded, as if he, too, had no idea. Something turned in his stomach, however, at the thought of the elevator stopping now, when Dean wasn’t with him. In a moment of terror, Dean realized that he and Castiel Novak were not actually in a relationship, and Cas could see as many people as he wanted. Mr. Novak arrived just as Dean swallowed back the lump in his throat.

He said something that Dean didn’t hear through his worry, but when Mr. Adler asked, “Did the elevator break on you again?”, Dean heard Mr. Novak’s answer clearly.

“Not at all,” he’d said. “I just took a moment to stop on the seventh floor. I apologize for being late.”

Dean looked up curiously, still trying to push down the jealousy he’d felt. Mr. Novak did not even look his direction, however, when he sat down at the head of the table. He opened his briefcase and immediately opened up the morning’s discussion topics.

As Mr. Novak spoke, it became clear to Dean by the looks everyone in the room gave to their boss that Mr. Novak was strongly admired by everyone. Just as Mr. Adler had explained on his first day, Mr. Novak really was the sort of boss that was approachable and genuine. For the first ten minutes, everyone seemed to be peacefully at ease while Mr. Novak spoke about the predicted costs, profits, and the programs that were going to be changing over this month. Then, suddenly, Mr. Novak spoke while looking down at a piece of paper on the table.

“Mr. Smith,” he said, not looking up.

“Yes, sir?” Dean answered quietly, hesitantly.

“Could you please come hand out these papers to everyone? These are our new forms for user registration, and I’d like everyone to get acquainted with them.”

Mr. Novak still hadn’t looked at Dean, and the uncomfortable spin of his stomach returned. Obediently, however, Dean stood. The plug shifted again and he braced himself against the table discreetly before walking toward the end of the table. When he arrived, Mr. Novak moved the stack of papers over for Dean to grab them while he ruffled through some more charts and diagrams in his briefcase. Dean grabbed the stack of papers with a clenched jaw. His plans to make himself irresistible to his boss were thrown out of the window.

After he’d handed a sheet to everyone, Mr. Novak nodded toward Dean’s chair, permitting him to sit back down. Dean took a deep breath, preparing for the plug to move again. When he sat, however, it didn’t shift a little bit. It vibrated.

Dean jumped out of his seat like he’d sat on a pinecone. Everyone turned to look at him, and Mr. Adler reached out to make sure Dean was alright. Dean, however, immediately turned red and looked at Mr. Novak.

Mr. Novak’s blue eyes were the only thing that gave him away. They twinkled. They actually twinkled with a cruel delight as he finally smiled at Dean.

“Something the matter, Mister Smith?” he asked pleasantly.

Dean almost laughed. The anxiety from before calmed down, and he was able to recognize that Mr. Novak was going to play with him during the meeting. This is how he would learn respect. He would learn to respect Mr. Novak in front of everyone, not in private. Understanding, Dean nodded, waved a hand, and grinned apologetically.

“Sorry about that, sir,” he smiled. “I think the seat was just lower than I expected.”

Mr. Novak laughed openly and waved a hand.

“Don’t worry about it, Mister Smith,” he said. “We’ve all been there, I’m sure. You should find an adjustment dial on the bottom of the chair.”

He reached back into his briefcase while Dean started to sit again, pretending to adjust the chair. By the time Dean’s rear reached the chair, the vibration had stopped and he was able to breathe easily.

“Now,” Mr. Novak said, “let’s continue.”

For the next thirty minutes Dean couldn’t concentrate. Mr. Novak reached into his briefcase another twelve times, and ten of those were a thinly veiled excuse to operate the remote to Dean’s vibrating plug. At one point, there was a five minute break where Dean was asked to help distribute pastries to everyone. For five entire minutes, Dean was sure someone would be able to hear the sound of the vibrations if he didn’t keep talking. He was forced to make conversation with Mr. Adler, and two minutes into it, Mr. Novak stepped next to them.

“How are you feeling, Mister Smith?” Mr. Novak grinned. His smile was even and steady, and Dean’s gut reaction was to smile as well.

“Good, sir,” Dean smiled. “We were just talking about you, actually.”

“That’s true,” Mr. Adler nodded. “Dean was saying how much he respects you. He said he hadn’t really seen you work your magic as the boss before, and it was impressive.”

“Really?” Mr. Novak wondered out loud. “Is this really the first time you’ve seen me as the boss?”

Dean coughed, suddenly choking on a small piece of pastry. For the next three minutes, the three of them enjoyed their break time before the meeting would resume. They spent it discussing the ideal pastry and beverage combination. Mr. Adler was strongly in favor of lemonade or another bitter drink with pastries. Dean was partial to protein shakes or herbal teas with them. Mr. Novak, of course, preferred to eat his pastries with hot coffee.

When the meeting resumed, the vibrations stopped again, and Dean sat down wondering how much longer the conference would last. In the end, it lasted long enough for Mr. Novak to reach into his briefcase six more times, making Dean squirm a little in his seat each time.

Eventually, there was nothing left to do. The meeting was over, and the employees were all enthused by their boss’s charisma. Everyone left the room in high spirits, despite it being early on a Monday morning. Mr. Adler was among the first to leave the room, saying he needed to get started on the program changes right away for the rest of the analysis team. Dean purposefully took time to carefully arrange everything within his briefcase so he would be near the end of the group. Finally, he looked up to see only four people left in the room – but none of them was Mr. Novak.

Dean’s brow furrowed and he bit his lip, wondering if he was supposed to leave the room. After a minute, he was the only one in the room. He waited a second longer to see if Mr. Novak would return, having conveniently left something behind, but that didn’t happen. The worry returned, and with it, nausea. Mr. Novak had said he’d stopped on the seventh floor. Could he be seeing someone else from the analysis department? Dean’s stomach churned.

He left the room frowning. The elevator ride was short, however, and he quickly masked his worry with a smile as he walked back to his office. He made it all the way to the secluded and private corner office before he realized someone was already inside. In fact, there was something different about the entire office. Slowly, Dean approached. He stopped in the doorway.

“Ah, Mister Smith!” Mr. Novak grinned. He spoke somewhat loudly. “I was hoping to find you here! I wanted to talk with you after you were such a good sport at our meeting. Do you have a minute?”

Dean hesitated.

Mr. Novak, who hadn’t noticed Dean’s discomfort until now, smiled with concerned eyes.

“Sure,” Dean finally answered. He walked inside and closed the door behind him. “What’s different about my office now?”

When he returned his gaze, Mr. Novak nodded to his right. There was a new cabinet installed to the side of the office. The cabinet looked like it was built in with the bookshelf that had always been there. The cabinet was tall and slender, and there was a silver lock on the front. Mr. Novak held out the key.

“Do you want to open it, Mister Smith?” he asked, still trying to judge what was wrong with Dean.

Dean hesitated again. He dropped his briefcase, reached for the key, and then sat down in the only other chair in his office.

“Is something wrong?” Mr. Novak asked quietly. He leaned against Dean’s desk.

“Is that why you were late today?” Dean asked. “You were making sure this was installed properly?”

Mr. Novak nodded. “I wanted to surprise you.”

Dean ignored the sincerity of Cas’s voice and instead said, “You weren’t stuck in the elevator with someone else?”

Mr. Novak’s eyes opened with comprehension. He smiled and his shoulder sagged like the very idea wounded him. Slowly, he stood straight, walked over, and made sure Dean was keeping eye contact.

“I was not with anyone else,” he said simply. “I won’t be with anyone else as long as I’m with you and able to make you happy. I only have one partner at a time, Dean.”

Dean bit his lip and scratched his elbow. Mr. Novak shook his head.

“I told you, Dean,” he said. “I’m very fond of you.”

“It’s just,” Dean finally said, “we aren’t in a relationship, so you’re allowed to see other people…”

“As are you,” Mr. Novak nodded. “As far as a relationship, we have a contract between the two of us, remember? I swore not to see anyone else without your explicit permission and approval, did I not?”

Dean barely remembered their agreements, he’d been so caught up in seeing what Mr. Novak could do. His muscles relaxed a little bit in his chair and he took a deep breath, looking at his boss calmly.

“There is no one else,” Mr. Novak said again. “You will always know if anything occurs that may affect our situation. Do you understand?”

Dean nodded slowly, trying to hide the disappointment that Mr. Novak had confirmed they were not more than partners. He hadn’t realized until now that he craved Cas and Mr. Novak. The soft, sweet person who called him a bee and petted his hair and the strong, rough person who made him feel so good in all the best ways. He wanted to belong to Cas, not just to Mr. Novak.

“Is there anything else you want to discuss? You still look a little worried.”

Dean buried his revelation and tried to think of their relationship the way that Mr. Novak did. This was about sex. Mr. Novak was the dom and Dean was the sub. That’s all there was to it.

“No, sir,” Dean answered. Even to himself, his voice sounded back to normal, like he was completely consoled.

Mr. Novak nodded, stepped away, and pointed at the cabinet again.

“Will you open this now?” he asked.

Dean grinned, nodded, and stood. He walked to the cabinet, pushed the key inside, and opened the door. When he saw what was inside, his jaw literally dropped.


	8. It's a Pillow...

**Summary for the Chapter:**

> It starts with a cabinet and ends with... well, you'll see.

**Notes for the Chapter:**

> kinks: FINALLY cockwarming. That's kinda it. Some discussion about Dean's comfort with the idea. Just a nice gentle chapter to give Cas the reassurance he needs. That's right. I said Cas. Doms need reassurance too, you know.

“Don’t speak. Just look.”

Dean stared, wide eyed. The cabinet was full of a mix of different things. There were small ropes, handcuffs, a small blue pillow and a matching blue blanket with brown leather edges, a box of different sizes and shapes of plugs along with bottles of different types of lube, three hangers for emergency outfits that Dean was supposed to keep at hand, a bag of chocolates, a slender blue tie, and – finally – a gift card to an electronics store downtown.

“I hoped,” Mr. Novak smiled innocently, placing a hand on Dean’s shoulder, “that you could use these for me, when I need you to. The gift card is specific, of course. You’ll need to take your phone there so a man named Ash can block each of our numbers from official records. Just as a precaution.”

Dean looked at a black rope near the back of the cabinet and realized it wasn’t a rope at all. It was a whip. He shifted his weight to his other foot and bit his lip discreetly.

“It’s not to be used all at once, obviously,” Mr. Novak explained. “I’ll tell you when to use them, or transport them to my office so I can use them on you.”

“I have to,” Dean started. Then he saw the dark look in Mr. Novak’s eyes and stopped. He hadn’t been given permission to speak yet.

“Also,” Mr. Novak continued, his voice somewhat rougher now, “you are welcome to use whichever plugs you like on any given day, but you will wear them while you are at work. I want to be able to visit you whenever I have the urge. Do you understand?”

Dean nodded, swallowing hard. He looked at the ropes and handcuffs and wondered how he could ever get them from here to Mr. Novak’s office upstairs.

“Any questions?” Mr. Novak asked. He was rubbing Dean’s shoulder softly, leaning closer so that his chest was pressed against Dean’s arm.

Dean nodded again. Mr. Novak grinned and clucked his tongue.

“I thought for sure that you’d speak after that one,” he laughed darkly. “I was hoping I’d be able to break in that whip today.”

Dean’s eyes fluttered back into his head for a minute. When he regained composure, he cleared his throat.

“Yes, Dean?” Mr. Novak whispered directly into Dean’s ear. “What are your questions?”

“Sir,” Dean started, trying to show how unbelievably on board he was with the new installation in his office, “I wondered how I should transport the items you request to your office from here. Won’t everyone see them?”

Mr. Novak simply smiled. He didn’t say anything for a minute before he tilted his head.

“There’s nothing in here that won’t fit in a briefcase, if you try,” Mr. Novak shrugged, like it wouldn’t bother him if Dean walked by the entire company holding handcuffs and a huge, pink butt plug. “You may also consider carrying them here.”

Dean jumped when Mr. Novak’s hand landed on the front of his pants.

“Whatever works,” Mr. Novak grinned simply.

Dean swallowed. Then he asked question number two.

“The pillow and blanket?”

Mr. Novak kissed Dean’s neck beneath his ear and stepped back. He straightened his jacket, reached down to pilfer one of the chocolates from the bag in the closet, walked around Dean’s desk toward his office door, and stood with his hand on the door handle.

“Bring them upstairs and you’ll find out,” Mr. Novak said quietly. His blue eyes scanned Dean’s body, eyeing his obvious erection, and then he opened the door. From the hallway just outside, he turned and said, “By the way, Mister Smith… I’m glad you finally see me as the boss I am.”

Dean flushed as Mr. Novak walked away. Quickly, he closed the cabinet and locked it, taking a moment to worry about what would happen if anyone opened it besides him. Then he took a deep breath, removed everything from his briefcase, and tried to make enough room for a small pillow and a blanket.

He should have waited to go up to Mr. Novak’s office. He knew he should have played with Mr. Novak’s mind and shown that he was just as stubborn as always, doing things in his own time. He would have, too… if he wasn’t so tremendously curious what a pillow could possibly be used for. Unfortunately, Dean was curious, and he quickly unlocked his play cabinet, grabbed the pillow and blanket, stuffed them in his briefcase, locked his cabinet again, and left his office, closing the door behind him.

No one stopped him on his way to the elevator, and the secretary on the eighth floor didn’t even look up when Dean walked by. Much to his relief, it seemed that none of his coworkers had x-ray vision. He was more than surprised, however, to find Mr. Novak’s curtains pulled away, and his office looking extremely open and friendly. Seeing that Mr. Novak was indeed alone in his office, however, Dean knocked on his door.

“Come in,” Mr. Novak said from his desk.

Dean stepped inside, closed the door behind him, and walked forward. Mr. Novak smiled at him with welcome. Without a word, he stood, rushed to the curtains, and closed them quickly. When the office was private once again, he walked over and pulled Dean in for a long kiss.

“Don’t get too relaxed,” Mr. Novak breathed around Dean’s lips. “The curtains will be open again soon.”

Dean’s brow furrowed, but he wrapped his arms around his boss, pulling at him to push his tongue further inside. Dean moaned around their kiss, shifting his hips until they met his.

“Needy today?” Mr. Novak teased, rubbing his hands along Dean’s ribs while they kissed.

He bit Dean’s lip and tugged it when he finally ended the kiss. At that point, Dean’s lips were swollen, puffy, and red. His eyes were lusty and curious, the green questioning Mr. Novak silently. Mr. Novak took a deep breath and nodded his head toward his desk.

“I have a lot of work to do today, Mister Smith,” Mr. Novak said simply. “I need to get a lot of things done. I can’t concentrate as well when I think of that plug you’re wearing for me, but I need to work. Do you see my problem?”

Dean nodded slowly. Mr. Novak was leading him by the hand to his desk.

“Will you bend me over now, sir?” he asked quickly.

Mr. Novak shook his head sadly. He reached over and slid his hand down Dean’s lower back until he grabbed Dean’s ass in his hand.

“Mmm,” he moaned quietly. “I want to, Mister Smith, but I have to work. Which leads me to the solution involving the pillow and blanket. Do you have them with you?”

Dean nodded, looking to where he’d dropped his briefcase. Before he could turn to retrieve it, however, Mr. Novak pointed underneath his desk. Dean looked at the space and back at Mr. Novak’s smile. He didn’t understand, so he looked at the area again.

Mr. Novak’s desk was large, of course. It was huge and wooden, and the area underneath his desk was roomy. The back of the desk covered the area from view from all other angles of the room, though some of the space reflected in the windows behind the desk. Dean’s eyes narrowed while he considered what Mr. Novak might have in mind, and then it clicked. His mouth opened and Mr. Novak laughed.

“I want you undressed, Mister Smith,” Mr. Novak nodded. He reached around and grabbed Dean’s ass with both hands. “I want you to keep that plug in for me for when I need to take breaks. You left your office door closed downstairs?”

Dean nodded, his mouth slightly drier than it was before.

“Good. No one should try to disturb you, and I will make sure they are all aware that you will be working late in your office today. Any calls that must be taken will be forwarded to your cell phone. You will be my cockwarmer today, Mister Smith, and whenever I call you in the future. Do you understand?”

Dean nodded slowly this time.

“You will not,” Mr. Novak said darkly, placing on hand under Dean’s chin and forcing eye contact, “make me hard. You are to sit there and keep me in your mouth silently for as long as I wish. It could be ten minutes or it could be several hours. If you do this well, you will be given a reward you can’t even imagine yet. If you fail to do this, you will face the consequences. Any questions?”

“The pillow,” Dean started.

“It is for you to either sit or kneel on, whichever is most comfortable for you. Since you will be naked, the blanket can be used to cover your mid-thighs or lower, unless I say otherwise.”

Dean smiled, clenching his muscles to hide his excitement. Mr. Novak was keen, however, and he laughed under his breath.

“Once you are settled, Mister Smith, I will open up the curtains to my office and continue working as usual. People may come inside, you understand. Tell me how you feel about that, Mister Smith.”

Dean bit his lip and thought about someone sitting two feet away from him, on the other side of the desk, while he held Mr. Novak’s cock in his mouth. The idea was exhilarating. Terrifying, of course, but incredibly exciting.

“I’m worried about it, sir,” he answered honestly, “but I’d like to try it.”

“Will you tell me if it worries you too much?” Mr. Novak asked seriously, gazing at Dean with kind eyes. “You do remember your safeword, right?”

Dean nodded, said, “It’s impala, sir. I think I’ll be okay, though, sir.”

Mr. Novak leaned forward to kiss Dean lightly. Then he said, gentler, “If it is too much and you need to stop while someone else is in the room, put your hands on my knees and remove your mouth. Then I will send whoever is here away immediately. Does that sound okay?”

“Yes, sir,” Dean said, sounding very much relieved.

“I’m going to ask you your color in a minute, Mister Smith, and I need you to be very honest with me. This was on the list of things you were open to trying, so we’re just testing it out right now. You don’t have to go along with it if it upsets you, okay?”

Dean nodded.

“What’s your color, Mister Smith?”

“Green, sir.”

Dean’s green eyes smiled and he reached up to loosen his tie to show how ready he was.

“I’ll check back with you in half an hour and we’ll go from there,” Mr. Novak said simply. “Oh! And before I forget, Mister Smith…”

Mr. Novak moved around Dean and reached into a drawer in his desk. The mirror with the flimsy wire stand was still in there, and he handed it to Dean.

“I want to be able to look down and see your beautiful ass whenever I want to,” he explained. Then he kissed Dean once more and walked over to the curtains. “Knock on the back of the desk when you’re ready, Mister Smith. Your clothes can go in my bottom drawer.”

 

It took the very flustered Dean almost four minutes to get completely settled. His briefcase even fit inside Mr. Novak’s desk drawer, so there was no evidence he had ever been in the room. When Mr. Novak sat down, there wasn’t even a reflection in the window behind him. Mr. Novak could look down at an angle, however, to see Dean’s ass resting on the blue pillow he’d placed on the floor. When he was seated properly, Mr. Novak discreetly unbuttoned and unzipped his trousers, pulling out his cock and balls for Dean.

“Remember what I said about rewards or consequences,” Mr. Novak said under his breath.

Dean caressed the back of Mr. Novak’s calves before gently lowering his head to the perfect position. He accepted his boss’s soft cock into his mouth with curiosity. After a few seconds, Dean relaxed and let the tension fall from his shoulders. His mouth filled with saliva, but he knew that swallowing would be a big mistake. Instead he focused on breathing slowly and quietly through the nose. Meanwhile, he heard Mr. Novak working industriously.

Time passed leisurely while Dean sat underneath Mr. Novak’s desk. The intimacy of having Mr. Novak in his mouth almost wasn’t even sexual. To Dean, it seemed almost religious. This was his act of piety, his display of faith. This was the strangest, and somehow best, way for Dean to show his dom how much he appreciated him. Dean closed his eyes and felt his heartbeat slow. There was a very faint pulse of the cock in his mouth, and it lulled him into a state of calm. Dean was more relaxed than he’d ever felt before, despite knowing that someone could walk into the office at any minute.

“What’s your color, Mister Smith?” Mr. Novak asked when thirty minutes had passed.

Dean grimaced when he was forced to let Mr. Novak out of his mouth for the second it took him to answer. As soon as he finished speaking, however, he replaced his head and heard the chuckle from above him. A hand reached down and ran along Dean’s head affectionately.

“You’re doing incredibly well, Mister Smith,” Mr. Novak smiled. “I have a scheduled meeting in five minutes, so remember what we talked about.”

Dean stroked the back of Mr. Novak’s legs gently to show his understanding, which earned him another affectionate rub of the head. Then, Mr. Novak went back to work.

Dean’s eyes were closed when he heard the knock on Mr. Novak’s door. He jumped a little bit, making Mr. Novak laugh as he said, “Come in, please.”

When Dean settled down again, he heard the other person enter the room, close the door behind them, and move to sit in front of Mr. Novak’s desk. Dean could sense that the person was sitting there, feet from Dean’s completely naked self, but he wasn’t concerned. In fact, he just closed his eyes and listened to the pleasant rumble of Mr. Novak’s voice as he spoke to the visitor. Affectionately, Dean gave the back of Mr. Novak’s leg a gentle rub before taking a slow, quiet breath. He could get used to this.


	9. Lunch Break

**Summary for the Chapter:**

> Just a short chapter with a lunch break.

**Notes for the Chapter:**

> No real kinks. Just affection, leading to a chapter that is gonna be very great.
> 
> Edit: actually, there are panties involved.

Dean remained underneath Mister Novak’s desk for several hours without pause. At one point, he found himself so calm that he almost fell asleep with his chin resting on the small area of Mr. Novak’s chair that was between his legs. Mr. Novak reached down every once in a while to give Dean some acknowledgement, but he mainly focused on working. According to the conversations Dean overhead in each of his phone calls and meetings, Mr. Novak often worked hard, taking no time for himself. Dean could hear the respect and admiration in each visitor’s voice as they discussed what changes should be made for the next month.

March was ending, and April would be there by the end of the week. Summer was a very irregular working time for the company. They did most of their planning through the winter, but summer work could be either very scarce or suddenly urgent. Summers were hard to pin down, so the company tried to encourage that anyone who took vacations with their family keep ready for emergencies.

For Dean, as he sat beneath Mr. Novak’s desk, his mouth open and drooling around Mr. Novak’s cock, thoughts of the summer unnerved him. Would they still be together then, he and Mr. Novak? Would Mr. Novak still call Dean into his office every once in a while? What if, by the time summer rolled through, Mr. Novak was finished with Dean?

Dean took a deep breath through his nose and sighed, pushing thoughts of the future from his mind. The important thing was that he was here now. At one point, Meg arrived in the office with a double lunch, as Mr. Novak had requested. On her way out, she closed the curtains at his request.

“Mister Smith,” Mr. Novak said, “you can come out now.”

Dean crawled out from underneath the desk stiffly. When he stood, he took a moment to stretch his legs and arms, turning his neck from side to side and cracking his knuckles. Mr. Novak smiled affectionately, gestured to the private bathroom, and then sat down on the couch to his own lunch. Dean quickly refreshed himself in the bathroom, remaining naked other than the plug that was still inside of him. He washed his hands thoroughly and brushed his teeth with one of the unopened toothbrushes in the cabinet there.

“Ah,” Mr. Novak said when Dean finally walked over. He’d just taken a bite from his sandwich and there was some mayonnaise on his lip that he quickly licked off. “You’re welcome to wear your blanket over your lap while you eat. I ordered a pita for you, by the way. I also have coconut water here for you.”

Dean grinned, walked over, and sat down on the ground by Mr. Novak’s leg.

“You can sit up here with me, Mister Smith,” Mr. Novak said, temporarily confused.

“I know,” Dean answered quietly. He leaned against Mr. Novak’s leg and reached for his lunch. They ate in happy silence, and afterward Dean insisted that he brush his teeth again before returning to his spot under Mr. Novak's desk.

 

The work day ended in ten minutes. If Dean could make it ten more minutes, Mr. Novak had promised him a great reward.

With five minutes left, Mr. Novak reached for his phone, dialed for his secretary, and said loudly, “Meg, you can go ahead and head home now. I believe I’ve had all of my scheduled meetings for today, so I should be wrapping up soon. Thank you.”

Then, he reached down and slowly moved Dean backward. His cock was wet from Dean’s mouth, so with one hand gripping the back of Dean’s head, Mr. Novak rubbed himself over Dean’s hair and face to dry off. As he did, he started to get hard. He looked down at an angle, seeing in the mirror that Dean’s plug was taunting him.

“You ready for your reward, my good boy?” Mr. Novak asked quietly.

“Yes, sir,” Dean answered, rubbing his face against the hardening cock pressed against it.

Mr. Novak smirked, rolled his chair backwards, tucked himself back into his pants, and zipped up. Then he walked out from behind his desk so he could close the curtains in his office and lock the door. Dean, meanwhile, knew better than to move without permission, though he couldn’t resist tempting fate. He curled one of his fingers so it hooked on the edge of Mr. Novak’s drawer. Slowly, while Mr. Novak was away, Dean looked in to see his pile of clothes. He pulled two things out of the drawer before closing it again. Mr. Novak didn’t seem to notice.

From the sitting area in his office, Mr. Novak said, “Come here, Mister Smith.”

It was time. Dean had been prepared to give Mr. Novak something he couldn’t resist, and so he crawled out from under the desk, stood, and turned. He faced Mr. Novak, his lips painted in glittery gloss. He set the heart shaped container on the desk in front of him and watched Mr. Novak perk up, watching with big eyes. When Dean stepped out from behind the desk, Mr. Novak’s mouth dropped.

They were pink. They were satiny. They had a little white bow at the top and mesh along the sides and rear. They looked good on him. Panties.

Mr. Novak’s face went reddish, a look that Dean had never seen before. Mr. Novak was surprised, and his eyes were devouring Dean. Unbelievably, however, he managed to keep his voice steady when he spoke.

“I guess I’m being rewarded, too,” he said. He licked his lips. Dean blushed, pleased that he could see the obvious reaction in Mr. Novak’s pants. Mr. Novak cleared his throat and said, “You will not take those off. Mister Smith, you will only wear panties to work from now on, do you understand?”

Dean nodded, grinning. Then, as the blood rushed to his own cock, he bit his lip. Mr. Novak almost ran forward – self control be damned. Instead, however, he managed to take a deep breath and point to the couch.

Before Dean moved, he asked, his voice purposefully low, “Will you fuck me now, sir?”

Mr. Novak, again, resisted the urge to drop everything and bend Dean over his desk. He would have slid those panties out of the way and fucked Dean so hard and fast that Dean would be screaming. He wanted to – God did he want to – but he waited. He unbuttoned his shirt and waited while the victorious Dean strutted over to the couch. He sat down elegantly, crossing his legs like a proper businessman, while he watched Mr. Novak strip.

“Will you do me a favor, sir?” Dean asked suddenly. Mr. Novak’s fingers stopped untying his tie to listen, his eyes looking up from Dean’s legs to his painted lips. “Will you leave the tie on?”

Mr. Novak’s hands fell and he pushed down his pants and underwear. He stood in front of Dean wearing nothing but the tie, watching Dean twirl his fingers around each other, waiting. Smugly, Dean looked up through his lashes at Mr. Novak.

“Your reward,” Mr. Novak said hoarsely, “was going to be a blowjob from me.”

Dean’s eyes opened wide. Mr. Novak had never even hinted at the possibility before, and Dean hadn’t minded. But the idea now hit him. Dean thought of those bright blue eyes looking up at him from between his legs, his hands stroking Dean’s chest and thighs while he took on the position he usually reserved for Dean…

“However,” Mr. Novak interrupted, “I think my plans need to change, because I am not taking those off of you right now.”

Dean blushed again and uncrossed his legs so his boss could see exactly how happy he was feeling.

“So, I will ask you, Dean,” Mr. Novak smiled. “How would you like to be rewarded?”

Dean bit his lip again and looked around the room. Then he blushed a deeper shade of red. Mr. Novak raised an eyebrow, tilted his head, and waited.

“Sir,” Dean finally admitted, “I need you to convince me that I belong to you alone.”

Mr. Novak’s eyes flashed and he stared, wondering how Dean could ever think he could belong to anyone else.

“You want to know that you’re mine?” Mr. Novak repeated.

Dean nodded.

“You want me,” Mr. Novak reiterated, “to hold you down on that couch and fuck you until you’re screaming that you belong to me?”

Dean looked from Mr. Novak’s cock to the blue tie on his naked chest to his darkened eyes.

“Yes, sir.”

Mr. Novak cracked a smile. In a second, he was in front of Dean, pulling him up roughly by his wrist, twisting it slightly in the process. Dean gasped, grinning.

“I think I can handle that,” Mr. Novak breathed.


	10. Marked

**Summary for the Chapter:**

> Mr. Novak shows Dean that he could only ever belong to one person...

**Notes for the Chapter:**

> whew. What isn't in this chapter? Okay...
> 
> kinks: marking, scratching, biting, rough anal sex, spanking, references to a little blood drawn from scratching and biting, manhandling, rough treatment?, hair-pulling, panties, lip gloss, coming so hard you black out (?) and possessiveness/ownership. Let me know if I should add anything else to the list.
> 
> Next chapter will be 100% fluffy aftercare! Don't worry, it's coming!

Mr. Novak tugged quickly on Dean’s wrist, pulling him forward against his chest. With one hand, he reached to pull Dean’s chin up. Mr. Novak’s mouth enveloped Dean’s, his teeth biting with no small amount of force onto Dean’s bottom lip. Then his tongue pushed into Dean’s mouth, his fingers clawing at the back of Dean’s neck, as he growled in the back of his throat. The vibrations made Dean’s legs weak as he stood against his boss, an arm held too tightly in front of him and his neck and spine scratched unceremoniously.

“You still doubt you’re mine?” Mr. Novak breathed. As soon as he finished speaking, he lunged in to bite Dean’s lip again. His teeth dug into the flesh while his tongue licked a stripe across it. “I’ll take care of that.”

Mr. Novak finally released Dean’s wrist, moving his hand instead to grab Dean’s ass. His fingernails dug into Dean’s skin, breaking it, and Dean gasped. Mr. Novak smiled, breathing heavily while his eyes flashed once again over Dean’s body leaning against him. Dean’s painted, glittering lips were the first target.

“Who gave you that lip gloss, Mister Smith?” Mr. Novak growled. He leaned forward and bit Dean’s lips again. “Who bought that for you?”

“You, sir,” Dean panted, his eyes closed tight as both of his lips were bitten and pulled and licked and sucked. He was sure there would be no gloss left in a minute.

“Complete sentences, Mister Smith,” Mr. Novak grumbled, Dean’s lip still between his teeth.

“You gave me the gloss, sir,” Dean whined. “Please.”

Dean clenched around the plug in his ass and then felt the sting of Cas’s hand against his skin. Cas had slapped his ass, and the heat pulled a loud, involuntary moan from Dean.

“Those lips are mine,” Mr. Novak nodded, “and so is the rest of you.”

Dean couldn’t help himself. He pushed his ass back into Mr. Novak’s grip, and he felt it squeezed again.

“Fuck me, sir,” Dean whimpered, “please. Please fuck me.”

Mr. Novak slapped Dean’s ass again before sticking a thumb in the band of the panties. His lips trailed down Dean’s neck, sucking intensely onto his throat.

“You’re mine,” Mr. Novak breathed. “I’ll decide when I want to fuck you. Do you understand?”

Dean nodded, his eyes tightly shut, and his breath coming in short gasps.

“I’m going to mark you now, Mister Smith,” Mr. Novak said, grazing his teeth over Dean’s neck. “What’s your color?”

“Green,” Dean said, his voice higher than usual.

Mr. Novak bit into Dean’s neck, just above the shoulder, hard enough to leave a mark for a few days. Then he sucked Dean’s throat again, leaving a trail of bruises from just below his chin, around to each of his ears, and down to his chest.

Mr. Novak shoved Dean’s shoulder and turned him around, pressing against his back with his cock. With Dean’s ass pressed against his cock, Mr. Novak moaned. Sucking on the back of Dean’s neck and his shoulders, Mr. Novak concentrated on thumbing over Dean’s nipples while Dean tried to regulate his breathing.

“Whose are these?” Mr. Novak asked, his voice deep and dark. He pinched Dean’s nipples. “Who owns these?”

“You, sir,” Dean said louder than he intended. Then he remembered his instructions and rephrased: “You own my chest, sir.”

“That’s right,” Mr. Novak said. “You’re mine.”

His hot breath against Dean’s shoulder make Dean’s eyelashes flutter. Mr. Novak’s hands slid down Dean’s chest and rested on his hips. He rubbed the area connecting Dean’s thighs to his hips, just under the hip bone. Then, he pressed the nail of his thumb into Dean’s hip, scratching until there was a bright red mark following his finger.

“Your lips are mine,” Mr. Novak said simply. “Your chest is mine. Your hips are mine. What else is mine, Mister Smith?”

“Everything’s yours, sir,” Dean breathed. His cock was hard, leaking into his panties. He rutted upward to try to get some friction, forcing a loud moan from his lips. “I’m yours.”

“You should be more specific, Mister Smith,” Mr. Novak replied, pushing Dean’s hips until Dean fell against the couch. “Tell me what’s mine, Mister Smith.”

Dean panted. Mr. Novak was manhandling him so that he was kneeling on the couch, his face pushed into the back cushions and his hands gripping the frame of the couch. Dean could feel the faintest brush of Mr. Novak’s tie over his back and he pushed his cock against his panties again.

“My, ah,” Dean cried. Mr. Novak slid one hand down Dean’s back and up to his neck. Then, he gripped Dean’s hair in his hand and pulled Dean’s head back. He waited. “My ass, fuck, sir. Ah, my ass. Fuck!”

Mr. Novak gripped Dean’s hip with his free hand, pulling his hair harder.

“What’s your color, Mister Smith?” Mr. Novak asked.

“Green, sir,” Dean said. Immediately, Mr. Novak slapped Dean’s ass. “Fuck!”

“I’m going to leave this ass red with my handprints, Mister Smith,” Mr. Novak said. “Is that what you want? You want me to mark your ass like I have the rest of your body?”

“Yes, please, sir,” Dean answered. “Please mark me!”

Dean reached up and grabbed the wrist of the arm that held his hair. He caressed the wrist with his thumb and waited for the spanking to begin. Finally, the first slap landed.

“You’re going to take this,” Mr. Novak said. He slapped Dean’s ass again. “You’re going to take as many slaps as it takes to leave you raw.”

Tears rose in Dean’s eyes and he tried again to get some friction against his cock. Mr. Novak slapped Dean again.

“Fuck!” Dean screeched. His voice was much higher than it had ever been, and he was so hard. It was so much, too much…

“Are you going to come from this, Mister Smith?” Mr. Novak taunted. “Are you going to come before I even fuck you?”

Dean shook his head against the grip in his hair.

“A good boy would wait to come until his master came,” Mr. Novak said, slapping Dean harder than before. “Who’s your master, Mister Smith?”

Dean shivered and whimpered loudly. Mr. Novak seemed to accept that as an answer, judging by his breathy laugh.

“Are you going to wait for me to come?” Mr. Novak asked.

Dean nodded, unable to process any thought or speech.

“Are you ready to be fucked, Mister Smith?”

Dean pushed his ass backward in answer. Mr. Novak stopped slapping his ass long enough to slowly pull the plug from Dean. Thankfully, Dean had refreshed himself a few hours before and reapplied lube. Mr. Novak wiped some of the excess lube from the plug onto his cock along with his own precome, pulled down Dean's panties just enough, and then he positioned himself.

“This is mine, Mister Smith,” Mr. Novak growled. “I want you to say it.”

Without warning, Mr. Novak pushed forward. He shoved his cock into Dean and then pulled out immediately.

“Yours,” Dean whined.

The tears fell from the corners of his eyes and he bit his tongue hard enough to draw blood. Again, Mr. Novak pushed forward completely, burying himself inside of Dean, before coming all of the way back out again.

“Complete sentences,” Mr. Novak barked, sounding like thunder behind Dean.

“I’m yours,” Dean cried, his eyes closed tightly. “Ngh!”

Mr. Novak pressed forward harder, shaking the entire couch and the curtains against the window.

“Ah!” Dean shouted. “Yes!”

Dean clenched around Mr. Novak and shifted his hips back and forth. Meanwhile, Dean’s cock leaked against his stomach, pressed there by his position kneeling on the couch. Mr. Novak shoved Dean’s face further into the cushion to stifle the shouts that continued from Dean’s mouth. Again, he pulled all of the way out before thrusting back inside.

Mr. Novak paused. Dean’s whining slowed and Mr. Novak allowed his face to lift off of the couch. He was sloppily covered in tears, his face as bright red as his ass. For the next few seconds, they could have heard a pin drop. Then, Mr. Novak leaned over Dean, his chest flush with Dean’s back, and he kissed Dean’s cheekbone.

“I want you to say it once more, Mister Smith,” Mr. Novak whispered, pressing more kisses against Dean’s heated face. “I want you to know that you’re going to have these marks for a week, and then we can do it all over again. You won’t go a day without some sign that you are mine. So, Mister Smith, I want you to tell me once and for all. Who do you belong to?”

“I,” Dean breathed heavily, sore and aching and tired. His cock grew painful, but he managed to control himself for a little longer. When he finished speaking, his voice squeaked and cracked. “I belong to you alone, Cas.”

Upon hearing his name, Mr. Novak’s eyes opened wide and he felt himself coming. Quickly, he regained composure and chose to ignore Dean’s mistake of addressing him with his first name. He doubted Dean would even remember having said it, anyway. As the shock left him, Mr. Novak pressed lightly forward and back, rocking against Dean until he panted hotly against Dean’s neck. Then, quickly, he reached down, grabbed Dean’s cock in his hand, and stroked it.

“Come, Dean,” Cas whispered, knowing that Dean would be passing out soon.

Dean wouldn’t remember, but Mr. Novak… Castiel… would always know how hard Dean came against his office couch, his body beaten and owned, completely submitted and spent. He would always know that Dean had come while shouting into the cushion, gripping onto it for dear life. He would always know that when Dean was at his limit, the only thing he could still say was, “Cas.”


	11. Rest

**Summary for the Chapter:**

> Cas takes care of Dean after a rough time together.

**Notes for the Chapter:**

> 100% aftercare. :)

Dean’s eyes opened almost immediately after they’d closed, but he was completely disoriented. He tried to focus his eyes and found that he was still facing the back couch cushion. Castiel was still settled inside of him, rubbing Dean’s back soothingly.

“I’m going to get out of you now, Dean,” Cas said quietly. “Do you want your plug back in?”

Dean’s mouth was open, but all he could do was grunt affirmatively. Cas smiled to himself, slowly pulled away from Dean, and gently replaced the plug, now lubricated with Dean’s cum from Cas’s hand. Dean whimpered happily when the plug was in place and his panties were readjusted comfortably.

Breathing heavily, Cas helped Dean fall back onto the couch, lying down lengthwise so he could sleep if he needed to. Cas ran his hands smoothly across Dean’s ribs and chest. Dean closed his eyes, breathed deeply, and began to feel the aftershocks of his orgasm fading.

“Oh,” he sighed. He remembered the stimulation, the heat, the desperation. He smiled widely and felt his eyes water. Contented, he opened his eyes. “Oh.”

Cas was smiling cutely, a look in his eyes that Dean had never seen before. Those blue eyes sparkled and spun like galaxies, blissed out and affectionate.

“You were so great, bumblebee,” Cas smiled, pressing a light kiss to Dean’s hand. “You were fantastic. I need to get supplies from the bathroom now to clean you up. Can I leave you for a minute now, or do you want me to wait a little longer?”

Dean swallowed hard.

“One minute?” he asked.

“One minute,” Cas laughed. “I promise.”

Dean nodded slowly, let Cas stand, and waited for him to come back. While he was gone, Dean looked down his body. He was covered in white, and his skin was red all over. There were wounds on his hips, and he suspected his neck as well, that bled lightly at the same time that bruises darkened. When he looked up again, he wondered how long Cas would be gone.

Then his stomach clenched and his breath stopped in his throat. Worry filled him and he vaguely moved his hand out, hoping to find Castiel there at his side. When he wasn’t met with Cas’s warm body, he breathed harder.

Just when the tears in his eyes spilled over, his bliss shifting slowly into terror, he felt a hand grab for his own. Cas kissed his hand, wrist, elbow, and shoulder.

“It’s okay, Dean,” Cas whispered apologetically. “I’m here. I’m back.”

Dean nodded.

“Breathe, Dean,” Cas said quietly. “Deep breath. Inhale and exhale slowly, okay? I’m here. I won’t let anything happen to you.”

Dean nodded, met Cas’s bright eyes again, and let some of his tension go.

“Let me take care of you now, Dean.”

Cas had brought a bowl of warm water, three clean cloths, and some antibacterial gel from the bathroom. He kneeled on the ground and inspected Dean’s face first. Then, with a secret smile on his lips, he dipped the softest cloth barely into the warm water. Dean’s lip was bleeding slightly, but the water would be enough to wash it clean.

“You were so good, bee,” Cas said gently, pressing the cloth against Dean’s cheekbones first. “You were perfect.”

Cas continued to praise Dean while he washed his cheeks, lips, and jaw with the warm water. When he reached Dean’s neck, he wiped it down with a second cloth before applying some Neosporin. The bleeding itself was so light that the gel placed over it was enough to stop the bleeding.

“When I finish your front,” Cas said, “I’ll need you to turn over. Do you think you can do that?”

Dean nodded slowly, watching Cas work over his chest. Cas was still wearing his tie around his neck, and Dean couldn’t help but grin.

“Of course you can,” Cas laughed. “You’re so strong, Dean. You’re so perfect.”

Dean let his eyes fall shut while Cas cleaned the rest of his chest, hips, and thighs.

“I think, though,” Cas was saying with amusement, “these panties might need to be cleaned professionally.”

Although the tip of Dean’s cock had breached the upper band of the panties when he came, some cum had still landed against the delicate material of the mesh siding. Dean peeked down at Cas and saw his happy grin. Cas’s teeth were showing while he smiled, and Dean reflected on how those teeth had marked Dean moments ago. Dean definitely belonged to his boss, but did his boss belong to him? Dean pushed the thought from his mind while Cas tended to Dean’s soft cock and legs.

“It’s time to turn over, honeybee,” Cas whispered, kissing Dean’s belly.

Slowly, Dean turned toward Cas, adjusting himself so that he was laying on his chest on the couch facing outward. Before Cas started cleaning Dean’s back, he kissed Dean’s nose.

“Thank you,” Cas smiled.

“Any time, angel,” Dean sighed.

Cas grinned, saying, “You must be feeling a little better now, huh?”

Dean nodded, feeling the warm cloth pressed to the small of his back.

“That was intense,” Dean said simply.

“It was,” Cas agreed. “You did so well, Dean, and I’m so proud of you.”

Dean blushed. Cas pulled Dean’s panties aside to clean his ass. He pressed the towel gently, soft as a kiss. Dean’s tension dissolved and he felt totally at peace. Cas was taking care of him. Cas knew what Dean needed.

“I loved your surprise,” Cas said. “Where did you get the idea to wear panties?”

Dean smiled mysteriously, staying quiet until Cas laughed under his breath.

“I always loved them,” Dean finally said quietly. “I hoped you would, too. If my aching is any judge, I’d say you did.”

Cas laughed, leaned down to kiss Dean’s ass, replaced the panties properly, and then kissed Dean again over the pink mesh.

“I do love them,” Cas said. “Thank you for sharing them with me, Dean. You’re so incredible, bee.”

Dean blushed, but let himself believe what Cas said. He closed his eyes and breathed deeper and deeper.

“Do you want to get dressed before you sleep?”

Dean shook his head. Then he mumbled, “Blanket?”

Cas laughed, stroked the back of Dean’s thigh, and went to retrieve the blanket. When he returned, he draped it over Dean and tucked it in along his body.

“I’ll sit beside you and wake you up in an hour, okay?” Cas whispered. Dean’s breaths were much deeper now, and very steady.

“Mhmm,” Dean said. “Thank you, Cas.”

“You’re welcome, Dean.”

Cas’s voice was far away, and Dean was warm and comfortable on the couch. He felt something rubbing his back, and he felt heavy. That’s when Dean moaned. One last sleepy sound escaped from his mouth, and Cas paused. It had sounded exactly like “love”.

 

When Dean woke up, Cas was still there, rubbing his back. He was dressed now, much to Dean’s dismay, and the sun was setting.

“You’re up,” Cas laughed. “I was just about to wake you.”

Dean groaned a little when he lifted his head.

“You’ll want to ice your neck and back a little bit tonight,” Cas said in answer. “Do you want me to stay with you tonight to help?”

Dean was about to refuse when he thought of something cheesy to say instead.

Touching the marks on his neck, he said, “You will be with me anyway.”

Cas grinned.

“I have a car downstairs for you, and they have instructions to walk you into your apartment. I also ordered dinner for you.”

Dean looked up, eyebrows raised. He sat up, wrapping the blanket around his waist. Then he realized how hungry he really was.

“Before you get dressed, I need you to drink something for me,” Cas said. “You blacked out a little when you came, so I don’t think you were hydrated enough.”

“Or,” Dean laughed, “maybe it was something to do with the hot guy fucking me senseless.”

Cas raised an eyebrow, shook his head, and handed Dean a water bottle.

“Drink, Dean,” Cas sighed. “Water is essential.”

“Yes, sir,” Dean said slyly, feigning innocence.

“You’re going home to rest, Dean,” Castiel said firmly. “You need to rest before we can play again.”

“Will we… play again tomorrow?” Dean asked hopefully.

Cas sighed. “If you’re in a good condition, we can. Keep in mind, however, that you do have an actual position here at Sandover and some work will need to be done tomorrow.”

“I think I’ve had a few different positions here,” Dean laughed. He stood and reached for his clothes, which Cas had folded and left on the coffee table.


	12. Impromptu Meeting

**Summary for the Chapter:**

> Dean is very (VERY) sore, but with Mr. Novak's help, he manages to relax.

**Notes for the Chapter:**

> kinks: really super gentle sex, affection, praise kink, marking kink kinda, panties (as usual), semi-public sex.. let me know if I missed anything!

Dean woke up with a lukewarm ice pack against his neck, the condensation wetting his pillow. He’d fallen asleep on top of it, with half of his Greek style pita left uneaten on his nightstand. He was completely naked in his house, wearing only a sheet so he would stay cool. Then his alarm buzzed to his right and he had to lift his arm to turn it off.

“Oh,” he wheezed. His arm was sore. When he managed to turn off the clock, he started to sit up. “Ah!”

Dean felt stiff and achy, and he rushed as fast as any other barely mobile person to view himself in the mirror.

“Oh, boy,” he whispered to his reflection.

His neck… all the way up to his ears and along his jaw, down his collar bone, and at his sternum… the entire area was a pale dark red. Bruised and bitten, he looked like he’d gotten into a violent clash with some kind of animal. Around his hips, too, the redness showed.

“Shower,” he told himself.

The shower was much longer than usual, only because Dean had to move very gently. With every motion, however, he remembered Mr. Novak rubbing his back while he slept on the couch, caring for him while he was asleep. Although the smiling made his jaw ache a little, he suffered through until he was able to step out of the shower and dry himself off.

“Right,” Dean squeaked.

He nodded to his reflection, clenched his ass just to feel how much it ached (a lot), and then walked over to his desk. Inside, for a reason he had long since forgotten, Dean found both liquid and powder foundation that matched his skin tone. He nodded at the makeup and slowly got to work making himself presentable.

It was close to time to leave when Dean could look at his reflection without seeing evidence of Mr. Novak. He had to keep his sleeves rolled down, of course, and he would not be able to bend over without risking his shirt coming untucked and revealing his hips, but all in all, he looked very professional. He slipped the makeup into his briefcase just in case.

Then he straightened his red tie, flattened his hair on his head, and walked out of the door to work. On the walk, he moved much slower than the other pedestrians. Although Dean needed to get to work as much as any of them, he physically could not move any faster. This earned him a few disapproving grunts and annoyed sighs from people who quickly tried to skirt around him on their way.

Finally, Dean arrived to his building, showed his badge to the security officer, and stepped toward the elevator.

“Mr. Smith!” Mr. Adler grinned happily. “I heard your door was closed all day yesterday! You must have been hard at work, as usual, huh?”

“Of course,” Dean answered, stepping to the side so Mr. Adler could walk with him into the elevator.

“It’s barely been two weeks and you’re already one of our hardest workers. I’ll be sure to let Mr. Novak know how well you’re doing.”

Dean smiled, nodded gratefully, and rode the elevator to the seventh floor. When he reached his office, he closed his door behind him. He opened the play cabinet, pulled out a bottle and a smaller black plug, and pulled down his pants. His green panties moved aside easily, and Dean was able to push the plug inside without any problems. Then, taking a deep breath, he put his pants back on, locked his cabinet, and opened his door again in an attempt to stay sociable.

Dean worked diligently for several hours before his stomach demanded lunch. Just as he stood to retrieve the leftover half of a pita from the night before, his phone rang.

“This is Mr. Smith,” he answered, wedging the phone between his shoulder and his ear so he could use his hands.

“Hello, Mr. Smith.” Dean’s shoulder fell, almost dropping the phone, because it was only Mr. Adler on the other end of the line. “I was wondering if you’d like to eat lunch with the department in the break room on four today. What do you think?”

Dean took a breath, reminded himself that he’d been too withdrawn lately and ignored his department too much, and then agreed.

“See you soon, Mr. Smith!”

When Dean dropped the phone, it rang again immediately.

“This is Mr. Smith,” he said again, less excited than last time.

“Hello, Dean,” Mr. Novak said roughly into the phone. “How are you feeling?”

Dean’s heartbeat increased.

“I’m very sore, sir,” he answered honestly, “but very happy as well.”

Mr. Novak laughed into the phone.

“Do you have plans for lunch?”

Dean hesitated. He really couldn’t afford to cancel lunch with his department. Team building was a key part of corporate life, and he needed to step up socially.

“Yes, sir,” Dean answered sadly. “My department is eating together on four.”

“Hmm,” Mr. Novak said into the phone. “I’ll have to make another arrangement, then.”

“I’m sorry, sir,” Dean panicked. “I could come up afterward, if you’d like.”

Mr. Novak just laughed, said gently, “That’s alright. I’ll come find you later, alright, Dean? Stay ready for me.”

Dean let go of an unsteady breath and nodded. “Yes, sir.”

 

“Exactly!” Beth snorted. She was hunkered defensively over her midday snack (strawberries, rhubarb cake, and chocolate chips fresh from the freezer) while playing a harmless game of cards with some others from the seventh floor. Next to her, Naomi rolled her eyes affectionately.

On the other side of the break room, Dean sat with several other employees and learned how to tell the difference between a cheap glass of wine and a proper glass of wine.

“The trick,” Crowley said authoritatively, “is in the packaging. The best wines come with very simple decorations.”

Mr. Adler nodded with interest and Dean swallowed his last bit of coconut water before standing to refill the container from the filtered tap.

“Oh no,” someone said. “It’s back to work already?”

Dean’s back was to the room while he filled his water bottle, but he turned to smile and wave to everyone as they left the room.

“Thanks for coming down today, Mr. Smith,” they grinned.

“Yeah, it was nice to see you around for a change!”

Dean nodded apologetically and wished them a good rest of their day. Then, he finished filling his water. As the last person in the room, Dean felt able to breathe easy. There was a mirror over the sink in the room, and he checked that none of his makeup had rubbed off on his suit. As usual, he looked very proper.

Then the door opened behind him.

“You look well,” Mr. Novak smiled, tilting his head.

Dean almost dropped his water bottle, but quickly regained his composure.

“Thank you, sir,” he answered eventually.

“I was hoping to be able to meet with you today, but my schedule is very full. Could you spare a moment now, Mr. Smith?”

Dean grinned. Then he looked around the room. Although they were the only two inside, there were several people shuffling around along the three windowed walls of the room.

“This room,” Mr. Novak explained quickly, “is often used as an impromptu business room, as I’m sure you were told when you first arrived. When all other conference rooms are full, this room is next in line. And, as it would happen…”

There was a pause while Mr. Novak closed the door behind him and locked it. He walked window to window and closed the blinds.

“…somehow, all other conference rooms have been filled for the hour.”

When the last set of blinds fell, Mr. Novak smiled happily at Dean.

“Now, Mister Smith,” he said seriously, though his eyes shined with joy, “I’m going to ask you again how you’re feeling. You will be very honest with me, do you understand?”

Dean nodded, set down his water, and walked up to his boss. When he was close enough to touch, Mr. Novak nodded, opening his arms to embrace Dean. He held him for several moments, kissed the top of his head, and stepped backward.

“How are you feeling, Dean?” he asked quietly.

“Sore,” Dean repeated his answer from earlier softly. “I’ve been moving very slowly, sir, and I expect to be in good condition again tomorrow.”

Mr. Novak narrowed his eyes at Dean’s neck suddenly. Then he licked his thumb slowly, dragging his tongue over the digit tauntingly, and pressed it to Dean’s neck. He wiped a small area of Dean’s collar, just where his neck and shoulder met. When he did, the makeup lifted and a small reddish patch of skin showed through. Mr. Novak laughed quietly when Dean huffed a little.

“That’s very clever of you, Mr. Smith,” Mr. Novak said. “For a moment I was concerned I hadn’t left enough of a mark on you yesterday.”

Dean blushed through the makeup. Slowly, Mr. Novak leaned down and kissed the red flesh he’d exposed on Dean’s neck.

“Can you take me yet?” Mr. Novak whispered into Dean’s ear, running his hands around Dean’s hips.

Dean closed his eyes and nodded.

“Slowly, sir,” he said, “yes.”

Mr. Novak leaned back, his happiness evident in his toothy smile, and he leaned forward to lazily kiss Dean’s lips.

“Would you like to lie down on the table, or stand?” Mr. Novak asked gently. He was quickly unbuttoning Dean’s pants.

“The table, sir,” Dean whispered.

Mr. Novak pushed Dean’s pants to the ground while nodding, only to step back in surprise.

Dean had obeyed his every order. Underneath his work clothes, he was wearing olive green panties with a black fringe. His cock was half hard in the panties, and Mr. Novak grinned happily when he noticed the rear was silken. Leaning around, Mr. Novak could even see that Dean had a small wet area of lube on his panties and a slight indent from his plug.

“You’re perfect for me, Mister Smith,” Mr. Novak couldn’t stop from saying.

After kissing Dean once more, as gently as a cloud touches a mountain, Mr. Novak helped Dean scoot onto the table and lay with his back against it. His ass was just barely off the edge of the table, but he was as comfortable as he could expect to be.

Gently, Mr. Novak traced Dean’s clothed cock with his finger. He swirled his forefinger around Dean’s balls and then along his crack. He continued until he could grip the back of Dean’s panties, pulling them down just enough so that his ass was exposed but his cock was still inside.

Having thought of everything, Mr. Novak reached into his suit pocket for a small tube. He set it on Dean’s stomach while Dean breathed slowly, relaxing as much as possible. He ached, but he wanted this – needed this – now.

“Color, Mr. Smith,” Mr. Novak said, his finger pressed onto the plug.

“Green, sir,” he answered immediately.

Mr. Novak slowly pulled the plug away from Dean, who sighed unhappily.

“Sh, Mr. Smith,” Mr. Novak scolded quietly. “We must stay quiet.”

Dean nodded, took a deep breath, and waited while Mr. Novak pressed a finger around the edge of Dean’s hole. He shuddered. The area still felt a little raw, but he didn’t care.

“I’m going to go very slowly, Mr. Smith,” Mr. Novak explained. “If you need me to stop, you will use your safeword. Say your safeword for me now, Mr. Smith.”

“Impala,” Dean answered obediently.

“Very good,” Mr. Novak nodded. “You will use it if you need to. I don’t want to hurt you, Mr. Smith. Do you understand?”

Dean nodded.

“Words, Dean,” Mr. Novak said even quieter.

“Yes, sir,” Dean answered, taking another deep breath.

Finally, Mr. Novak grabbed the tube from Dean’s stomach and opened it. With on hand, he unzipped his pants, pulled out his cock, and stroked it a few times. Then, he applied even more lube than he usually would. He made sure to get some on his fingers as well. Gently, and much too slowly for Dean’s liking, Mr. Novak pressed two fingers into Dean. Dean’s back arched slightly. Satisfied, Mr. Novak added another finger, at which point Dean whined quietly.

“I did not tell you to be silent, so as long as you remain very quiet, you are allowed to make noises,” Mr. Novak said. “I’m being very lenient with you right now, Mr. Smith, because you’re feeling so sore.”

“Thank you, sir,” Dean whispered automatically, smiling with bright eyes up at the man who had three fingers moving around his ass.

Mr. Novak leaned down one more time, kissed Dean’s lips and the red portion of his neck, and then removed his fingers. Torturously slowly, Mr. Novak pressed his cock against Dean, moving into him little by little. When he was inside halfway, Mr. Novak leaned over Dean to kiss him again, whispering praises to him.

“You’re doing so well,” he whispered, kissing Dean’s temple. “You’re so good for me – so perfect.”

Gently, Mr. Novak’s hips pulled away before pushing back. He was moving incredibly slowly, with a restraint Dean couldn’t even begin to understand. With every other push, Mr. Novak barely hit Dean’s prostate, at which point Dean whimpered happily.

Still whispering, Mr. Novak alternated between kissing Dean’s lips and neck while he moved slowly back and forth, never fully leaving Dean and never fully pushing inside. Dean’s brows furrowed and he tried to bite back any noise, but he panted loudly into Mr. Novak’s shoulder.

“Ngh,” Dean whined.

To cover the sound, Mr. Novak pushed his lips onto Dean’s. Slowly, they continued, and Dean had never known that sex could be such a relaxing event. He felt his tension leaving his body, and all of his worries faded. The only thing on his mind was the hope that he was good enough for Mr. Novak to come.

“So good,” Mr. Novak said around Dean’s lips. “You’re so perfect.”

The pace picked up then, and Mr. Novak accidentally grunted when he realized he needed more. Dean, too, had come to the same realization, and he arched his back, clenching around Mr. Novak as much as he could.

“Ah,” Mr. Novak said, kissing Dean’s temple again. He kissed down Dean’s face while he moved quicker and quicker. He kissed the crow’s feet by Dean’s smiling eyes, he kissed the flushed cheekbones of Dean’s blissful face, and he kissed the makeup covered jawline that Dean enjoyed so much. “Yes.”

The speed picked up, and Dean felt the stretch burn a little. He was still very sore, but at the moment, his pain was twisted undistinguishably with his pleasure.

Finally, Mr. Novak moved sporadically. He was close, and Dean knew that he, too, could come in moments. Sensing this, Mr. Novak reached down for Dean’s cock, grabbing it and swirling his still lubed fingers around the hard flesh.

“Whenever you want,” Mr. Novak permitted. “Come when you want to. Whatever you want.”

Dean reached up for Mr. Novak’s neck, pulling him down for another kiss while they worked together. When Dean came, both his ass and mouth were full with Mr. Novak, and he moaned contentedly into his boss’s mouth. Soon afterward, Mr. Novak came, spilling into Dean with a stifled grunt. They continued pushing and moaning against each other, Dean’s mouth completely resigned to Mr. Novak’s engaging tongue. Eventually, Mr. Novak pulled away, breathing hotly over Dean’s face.

“Thank you,” Mr. Novak said, kissing Dean’s neck again. “You’re so perfect, Dean.”

 

Cleaned up and perfectly professional once again, they both left the lunch room. Mr. Novak held the door for Dean with a smile, and Dean nodded appreciatively. Then they rode the elevator up, holding hands for a private moment. When they reached the seventh floor, Dean adjusted his tie, walked to his office, and found the makeup from his briefcase. Shaking his head with grumpy but blissful eyes, he closed his office door just long enough to cover up the two new red marks on his face and the one Mr. Novak had revealed purposefully.


	13. As Scheduled

**Summary for the Chapter:**

> The rest of the week goes well, but on Monday, Mr. Novak gets unpleasant news about his favorite employee.

**Notes for the Chapter:**

> hurt/comfort? dean's sick and cas takes care of him, cas is so concerned over the common cold and it's adorable, fluff

The week passed slowly. Even when Dean felt back in tiptop shape, Mr. Novak handled him gently.

“I won’t break, sir,” Dean had pouted at one point. “Don’t you trust me to handle it?”

Mr. Novak had promptly swatted his ass and growled into his ear.

“I decide when and how I want you, Mr. Smith.”

Dean had been silenced, and they’d continued gently fucking for the next few days. This did nothing to help Dean’s problematic infatuation with his boss. The gentle side of his dom excited him just as much as the rough side did now, and the fantasies Dean had when they were apart became less zealous and more sensual.

Eventually, the weekend arrived, and Dean spent most of his Saturday sitting on his couch watching cartoons. He typically worked out on Saturdays, but something seemed off. In fact, when he rested his head on his pillow that night, his eyes immediately popped open. That was when the cough began.

On Sunday, Dean drank several glasses of kiwi water, lemon cucumber water, coconut water, and sparkling water, hoping that he could wash away whatever cold he’d picked up. Unfortunately, the only change was an increased need to urinate.

Monday morning’s alarm clock woke him up as usual. It was the fourth of April already, and Dean’s cough was certainly gone, but his eyes could barely focus and his forehead was sweaty with fever. For ten minutes, he debated with himself before he picked up his phone. He had to call in sick for the first time since he’d been hired.

 

Mr. Novak worked as hard as ever that day, and all of his tasks for the day were complete long before lunch. He checked again on the monitoring software to see if Mr. Smith was signed into his company account yet, but the tab was still marked as inactive. Mr. Novak frowned, dialed, and waited for someone to pick up the phone. When they did, he frowned again.

“Mr. Adler?” Mr. Novak said into the phone. “Have you heard from Mr. Smith recently? I was hoping to meet with him today, if possible.”

“Oh, he called in sick this morning,” Mr. Adler nodded sadly. “There’s a definite something missing since he’s gone, too.”

“Did he say how he was ill?” Mr. Novak pressed suddenly. He loosened his tie around his neck and stood, holding the phone tight to his ear.

“I think it was a cold,” Mr. Adler explained. “He said he should be fine by midweek.”

“Thank you,” Mr. Novak said. Without waiting any longer, he dropped the receiver, picked it up again, and dialed his chauffer.

A few minutes later, he shut his office door behind him and walked to Meg’s desk on his way to the elevator.

“Where’s Naomi?” he said quickly.

Meg was startled, but she answered right away with, “She’s in conference room one, waiting for a civil engineer to meet with her.”

“Thank you,” Mr. Novak nodded, turning around and heading to the glass meeting room on his floor. Naomi was the only person in the room so far, so Mr. Novak didn’t hesitate. He walked inside and spoke in a rush. “You have children don’t you, Naomi?”

Naomi looked at him wide eyed and confused.

“Yes, I do. Is something wrong, sir?”

“No, of course not. I mean, not with them.” Mr. Novak rubbed the back of his neck, took a deep breath, and said a little shakily, “I need your assistance.”

“Of course, sir!” Naomi answered, seeming honored that the company CEO came to her for help. “What can I do for you?”

Flustered, Mr. Novak said, “I need to know what to do to care for someone with a cold.”

The amusement in Naomi’s eyes couldn’t be missed, but she managed to keep humor from her voice when she answered.

“Well, usually a cold goes away by itself in a couple days with plenty of rest. Soup and medication can help, if it’s needed. How bad is the cold?”

Mr. Novak opened his mouth, closed it again, and then grabbed a pen from his jacket pocket.

“I’ve heard that soup helps,” he agreed vaguely. “What kind of medication?”

Naomi listed off a few names of over the counter drugs that could help with the symptoms of a cold, all while wondering who Mr. Novak was so worried about. He had never had children, she knew, and his family didn’t have any young to take care of. Either way, seeing him so uncharacteristically ruffled over such a simple illness was pretty adorable in her eyes.

“Thank you Naomi. I truly appreciate this,” he finally said, replacing his pen in his pocket.

“You’re welcome sir,” she answered, still bewildered. With a maternal shake of her head, she added, “The key to curing a cold is rest, Mr. Novak. Be sure the patient isn’t doing anything stressful.”

On his way out of the room, Mr. Novak nodded to the civil engineer who was walking into the room. When he rushed back to Meg’s desk, he startled her a second time.

“Meg!” he said, making her jump. “Cancel all my appointments for the rest of the day. I have an emergency and will need to leave within the hour.”

Like Naomi, Meg found it refreshing to see such a usually calm and composed person behaving so irrationally. She was concerned, of course, but she couldn’t hide her smile when she responded to him.

“Sure thing, boss. Is everything okay?”

“Someone is ill,” he said with a wave of his hand. “Okay, here’s what I need you to do for me. Take this list down to the pharmacy and pick up all the items here. If there is anything else you feel is necessary, pick that up as well.”

“Yes, sir,” Meg answered. “What is this person ill with?”

“A cold,” Mr. Novak said, with an inordinate amount of worry. Meg bit her lip to hold back a smile. “Make sure you buy magazines as well. Any kind of magazine will do, I think, especially health food or cars. Then call my apartment and have Mrs. Tran pack a bag with my softest blankets and have her leave it with the doorman. I called my driver and he should be there to pick it up in twenty minutes; make sure she’s ready for it.”

“Of course,” Meg said, not even hiding her laughter.

“Half an hour Meg. You have half an hour.”

“Boss, it’s going to be okay,” Meg said reassuringly.

With a small smile, Mr. Novak nodded and rushed to his private elevator.

Over his shoulder, he called, “Thank you Meg!”

 

Almost an hour exactly after waking up, Dean heard a knock on his door. He set down his cup of tea on a coaster by the couch, found the door handle, and pulled it open.

“Oh,” he wheezed. His nose was plugged, and he was wrapped in a comfortable, gray bathrobe. He wasn’t wearing any socks or shoes, but his feet were flushed red with warmth. His cheeks, too, flamed red, although that could only be blamed partly on the fever. The rest of the fault resided with the man standing in Dean’s doorway holding two very full totes and an unbearably worried expression. “Cas?”

“Dean,” Castiel breathed. “I heard you were sick, so I brought aid.”

Dean’s eyes narrowed. His mouth was open so he could breathe properly, and his eyes were bleary and unfocused. He looked like he might tip over.

“Let’s get you inside,” Cas said awkwardly, ushering Dean into his own apartment. Cas closed the door behind him, latched the lock, and tried to find the kitchen.

Dean’s apartment was beautiful. The walls were painted white and yellow and brown, and some rooms had green and white wallpaper edging around the top. There were several windows, because Dean owned a corner apartment, and there were four rooms off of the hallway. On the right were two doorways leading to a living space and a bedroom. Directly ahead was a doorway to a bathroom. To the left, a single wide doorway led to Dean’s kitchen area, with a large dining space for entertaining.

Cas thought about complimenting the place, but then Dean swayed in place. Cas held onto Dean’s arm, bags still in his hands, and led him to the kitchen. Inside, he helped Dean sit on one of four chairs around a breakfast nook. Cas smiled when Dean’s robe slipped open a little bit before he helped fix it.

Finally, Cas set the bags onto Dean’s counter.

“Shouldn’t you,” Dean started to say. He coughed into his elbow for a full ten seconds before continuing. “Shouldn’t you be at work?”

“I told you,” Cas answered easily, “I heard you were ill. I was concerned, so I took the rest of the day off. I expect you to be fully recovered by tomorrow.”

Dean frowned.

“Hush,” Cas said, pointing at Dean with a fuzzy blue blanket he’d pulled from the bag. “I know I’m not the boss of you right now, but you’re still going to get better soon.”

“Why?” Dean asked.

“Because I,” Cas said.

He stopped with his mouth open. It hit him that he had intruded into an employee’s private apartment without permission, that he had abandoned a day of work and meetings important to Sandover as a company, and that he had done it all because Dean Smith was mildly sick. He wasn’t supposed to care this much when they weren’t playing, he thought. Dean was just someone to help relieve tension. It was a mutually beneficial relationship they had, and it was purely business.

So why was Cas unpacking cartons of ice cream, tubs of soup, bags of oranges, and bottles of medicine inside of Dean’s home?

Dean watched an internal struggle playing over his boss’s face with amusement. He’d never seen Mr. Novak so shaken. That he could be so worried for Dean… that must mean it was more than just sex, right?

“Because I can’t concentrate without you there,” Cas shrugged nonchalantly. “Now, we’re going to the living room, and we’re going to watch a movie so you can rest. You go in there and wait while I warm up this soup. I’ll bring it in to you and start the movie when I do.”

Dean hesitated, a warm smile on his lips.

“Go,” Cas said, pointing to the living room with a pot he’d found in the cupboard under the kitchen island. “You need to rest so you can work tomorrow, as scheduled.”

**Author's Note:**

> Thank you so much for reading! Please leave comments if you'd like (they make my day!).


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